Homeowner · NJ/PA · Member since 2026 · 1 post · 4 votes
My wife and I are new to BiggerPockets and excited to finally get started in real estate investing. We have talked about it and researched properties for years, but we never felt ready to take the leap. Now we are in a good position to move forward and are trying to figure out the best place to start.
We already own a vacation home and are thinking about trying it as a short-term rental. We are also considering buying another property in Pennsylvania to use as an STR. If anyone has suggestions for areas in Pennsylvania that are good for short-term rentals, we would love to hear them.
We are not sure whether it makes more sense to start with the vacation home we already own or buy a separate investment property. We would really appreciate any advice from people who have been in a similar situation. What worked for you, and what do you wish you had known when you were starting out?
Banker · Nationwide · Member since 2020 · 2k+ posts · 1k+ votes
2w
Marc,
Welcome to the Bigger Pockets community! Sounds like you might live in NJ and thinking about buying another REI in PA. First question would be have you explored or looked into Top States for STR? PA is not really a bad start but not the best in regard to "Amenity State" and Non-Seasonal. When I say Non-Seasonal I mean Florida for example all year long Hot, Cold, Warm January through December Non-Stop rental income.
You also have other States like NC/SC, TN, Texas that tend to be a little higher on the Top list. In most cases investors choose an adjacent state due to drive time or travel time to get to the property. To reduce the risk or stress you can amp up the property management company, buy renovate and get rent ready or buy turn key.
When property is less likely to have issues and is more turnkey its more stress free. Great thing about buying a Vacation home is less money down and can rent it out day one. I would focus on a daily rental to cash in on the ever growing "ADR" average daily rent rates. Again like I mentioned Florida certain places are approved for ADR and as long as you follow the purchase to cash flow ratio you're good!
If you ever have any questions feel free to check out my profile and reach out or send me an email.
Lender · Denver, CO · Member since 2021 · 41 posts · 11 votes
1w
@Marc Foti Welcome to BP — and congrats on being in a position to actually pull the trigger after years of research. That patience usually pays off because you're not walking in blind.
On your actual question — existing vacation home vs. new PA property — I'd push back gently on how you're framing it. These are really two different decisions with two different risk profiles, and conflating them can slow you down.
Converting the vacation home to an STR: This is the lower-risk, faster path. You already own the asset, you presumably know the area, and you're not taking on new debt or diligence risk. The real questions are: (1) Does the local jurisdiction actually allow STR permits, and is there a cap or waitlist? Some markets have gotten aggressive about restricting new STR licenses in the last couple years. (2) Does the property's layout/location actually support strong STR demand, or was it bought for personal enjoyment, which doesn't always mean rentable? I'd start here first — run the numbers on what it could realistically gross, check local regs, and treat it as a live test of whether you two even want to be STR operators (dealing with guests, turnover, dynamic pricing, etc.) before you go add a second property.
Buying a new PA property: This is a bigger swing — new debt, new market, new due diligence. STR performance is hyper-local; "Pennsylvania" isn't really a market, it's dozens of them with wildly different demand drivers. A few areas that consistently come up for STR activity: the Poconos (established vacation demand, but watch for oversaturation and township-level STR ordinances — some Pocono townships have gotten strict), areas near Gettysburg (steady tourism/history draw), and spots near state parks or lake regions (Deep Creek is actually MD but a lot of PA buyers look at that corridor too). Before you fall in love with a market, pull actual STR performance data (AirDNA or similar) for the specific zip code, not just "the region" — and call the township/county directly about STR permitting. Regs change fast and vary block to block in some of these areas.
My honest take: get the vacation home converted and running first. It de-risks the "do we even like doing this" question with capital you've already deployed, and what you learn from operating it (guest management, seasonality, actual vs. projected returns) will make you much sharper buyers when you do go shopping for the second property.
I've been on both the investing and the lending side of real estate for a while now — flipped and built spec homes myself, and spent the last 15 years in private/hard money lending, so I've watched a lot of new investors' first 12 months up close, good and bad. Happy to be a sounding board as you two work through this — no agenda, just glad to help fellow BP members think it through.
Attorney · 10451 Mill Run Cir #755 Owings Mills, MD 21117 · Member since 2024 · 300 posts · 113 votes
1w
Quote from @Marc Foti:
My wife and I are new to BiggerPockets and excited to finally get started in real estate investing. We have talked about it and researched properties for years, but we never felt ready to take the leap. Now we are in a good position to move forward and are trying to figure out the best place to start.
We already own a vacation home and are thinking about trying it as a short-term rental. We are also considering buying another property in Pennsylvania to use as an STR. If anyone has suggestions for areas in Pennsylvania that are good for short-term rentals, we would love to hear them.
We are not sure whether it makes more sense to start with the vacation home we already own or buy a separate investment property. We would really appreciate any advice from people who have been in a similar situation. What worked for you, and what do you wish you had known when you were starting out?
Welcome to BiggerPockets @Marc Foti! since you already own the vacation home, I would look at that property first before taking on another purchase. I've worked with owners who were excited to start renting a property and focused mostly on income, but the bigger questions showed up around the mortgage, insurance, HOA rules, local STR rules, and how the property was titled. Turning a personal-use property into a rental can change more than just how you use it.
I would want all of that checked before the first guest ever books. If the numbers work and the property can legally be used the way you want, your current home can also give you a much safer way to learn what you like and do not like about running an STR before buying another one. Since you are looking at Pennsylvania, I would also have someone local confirm the rules for the exact town or township, because those can vary a lot from one area to another.
CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
1w
Marc, since you already own a vacation home, I'd start by comparing using that property as your first STR versus buying a completely separate investment property before taking on more capital and complexity.
The biggest thing to look at is how often you and your wife currently use the vacation home personally. Once a property has both personal use and rental use, the tax treatment can get more complicated because the vacation-home rules may limit how expenses and losses are handled.
If you decide to turn it into an STR, I'd track the rental activity carefully from day one: average guest stay, your own participation, cleaner/co-host/manager hours, furnishings, improvements, and the placed-in-service date.
If the goal is eventually to use STR losses against W-2 or other active income, simply renting it short term isn't enough. The average stay and material participation tests matter, and personal use can also affect the outcome.
I’d also compare the existing vacation home against a new purchase based on actual after-tax economics: expected revenue, management, cleaning, utilities, maintenance, insurance, depreciation, and how much additional capital each option requires.
Starting with a property you already own can be a good learning opportunity, but only if the personal-use and rental-use rules still make the numbers work.
Feel free to DM me, I’d be happy to send over a few resources that might help you compare both options.
Banker · Philadelphia · Member since 2009 · 2k+ posts · 629 votes
1w
Welcome to BiggerPockets, Marc! You’re actually in a great position because you already own a property that could give you an opportunity to test the STR model before taking on another acquisition.
Before buying another property, I'd consider analyzing your existing vacation home as if you were purchasing it today: realistic nightly rates, occupancy, seasonality, management/cleaning costs, taxes, insurance, local STR regulations, and projected cash flow. That experience can teach you a lot before committing additional capital.
For Pennsylvania, there are definitely STR opportunities, but municipality matters just as much as the market. The Poconos and other vacation-driven areas can be attractive, but regulations, permitting, taxes, HOA restrictions, and even financing can vary significantly from one property to another.
One thing I wish more new investors understood is that you don’t have to know everything before doing your first deal—but you do need to underwrite the downside, understand your exit strategies, and surround yourself with the right professionals.
Since you’re investing in NJ/PA, happy to be a resource as you start evaluating properties and financing options. Welcome to the community!
Realtor · Boonton Township, NJ · Member since 2013 · 2k+ posts · 1k+ votes
1w
Hi @Marc Foti House Hacking can be a great way to get started. You need a place to live so why not live in one unit and have tenants pay a large portion of you mortgage while you live onsite. My wife and I started house hacking over 10 years ago, this decision alone has hands down given us the most freedom to do as we please. Be part is buy properties becomes easy as down payment can be as little as 3.5% each time you buy. We have purchased 4 properties using low money down loans, each time we leverage the property we are living in to buy the next. Happy to chat house hacking New Jersey anytime, all the best.
Lender · Colorado / New Mexico · Member since 2024 · 27 posts · 6 votes
1w
Welcome! I started out house hacking about two years ago. My first property was a single-family home with a mother-in-law suite, and after that I moved into a triplex.
I was definitely nervous getting started, but looking back, my only regret is that I didn’t start sooner. It’s been a great experience—not just financially, but also from everything I’ve learned and all the people I’ve met along the way.
Since you already own the vacation home, I'd personally look pretty hard at testing that as an STR before buying another property. It could be a good way to learn the business with an asset you already have while you figure out what you like and don't like about short-term rentals.
Lender · Licensed in 28 States · Member since 2026 · 119 posts · 30 votes
1w
@Marc Foti Congrats on taking the leap! Before buying another STR, it may be worth looking at the equity and financing options available on your vacation home. The right lending strategy could help you grow without tying up all your cash. If you'd like to explore your options, feel free to reach out. Happy to help!
Real Estate Agent · West Chester, PA · Member since 2017 · 266 posts · 94 votes
1w
I help people invest in the philly burbs, and I am friends with one of the owners of bespoke stay. He told me a few years ago that Ardmore was working well. Maybe try talking to them and getting some advice, and I am happy to help you execute. Or you could talk to other STR managers in the area and get their perspective. They know the ins and outs.
Real Estate Agent · The Emerald Coast · Member since 2017 · 254 posts · 99 votes
5d
Great points, Jason! I'm based along Florida's Emerald Coast, and I definitely agree that location and property management can make a huge difference in the success of a short term rental. One thing I'd add is that even within Florida, performance can vary significantly by neighborhood, property type, and local rental regulations. I always encourage investors to look beyond projected rental income and really dig into occupancy trends, seasonality, insurance, HOA restrictions, and operating expenses before making a decision. A property that looks great on paper isn't always the one that delivers the strongest returns!
Englewood, NJ · Member since 2018 · 356 posts · 60 votes
4d
Marc, welcome. I'm up in Englewood and I invest in Broward County FL tax deed auctions, so I'll offer a different angle than the others here.
Everyone's telling you to test the vacation home first - and they're right. But here's something worth considering: you don't have to choose between the vacation home and buying on the MLS. There are other acquisition channels most new investors never look at.
In Florida, tax deed auctions let you buy properties for well below market. The catch is it's cash-only, you need to research the property thoroughly beforehand (liens, occupancy, condition), and there's a redemption period to navigate. But the math can work incredibly well if you do your homework.
For your STR question specifically - the regulation piece is where most new STR operators get burned. Every municipality in PA writes their own rules. Some townships in the Poconos have moratoriums on new STR permits. Others require a primary residence test. Before you commit to any market, literally call the township office and ask "can I get an STR permit at this address?" Don't rely on what other investors tell you - regs change constantly.
One more thing: since you already own the vacation home, run the numbers on converting it BEFORE you start shopping for a second property. If the STR income covers the carrying costs plus a margin, you've got a self-funding test. If it doesn't, you just saved yourself from buying a second property with the same problem.
Banker · Philadelphia · Member since 2009 · 2k+ posts · 629 votes
16h
Welcome to BiggerPockets, Marc! You and your wife are in a good position because you already have a vacation property that could give you an opportunity to test the STR model before taking on another acquisition.
I'd start by running the vacation home as if you were evaluating it as a new investment: realistic nightly rates, occupancy and seasonality, management and cleaning costs, insurance, local STR regulations, and your true net cash flow.
If you start looking at Pennsylvania, don't focus solely on where STRs are popular. Pay close attention to municipality and HOA restrictions, property taxes, seasonality, and—most importantly—the backup plan. I always like to ask: If the STR strategy doesn’t perform as expected, can the property still work as a mid-term or long-term rental?
The same thinking applies to financing. Understand your purchase, operating, and eventual refinance numbers before you buy rather than trying to figure out the exit afterward.
I work with investors throughout NJ, PA, and nationwide on STR, DSCR, BRRRR, and other investment-property financing, and one thing I've learned is that there is rarely one "perfect" strategy. The better approach is finding the property and structure that fit your goals, risk tolerance, and exit strategy.
Best of luck to both of you, and welcome to the community!
