All Forum Posts by: Jason Regan
Jason Regan has started 19 posts and replied 297 times.
Post: Biggest business lesson you learned in 2k22?

- Investor
- Leominster Ma
- Posts 305
- Votes 162
@Kyle Curtin Here is my biggest lesson learned from last year. This is real estate related but not. I learned that we have to put out into the world what we WANT to happen not plan on what we think SHOULD happen. You know my story man. I was thinking too small and because of that wasn't achieving what I wanted. Since I changed to WANT and also told people my vision; the world is bringing my opportunities to make it happen. LFG KYLE!
Post: STR booking for others??

- Investor
- Leominster Ma
- Posts 305
- Votes 162
Hey @Henry T. I also book in Fl. I have no problem if an adult books for their kids. I do reach out to the adult to let them know they are FINANCIALLY responsible for their kids there. That usually gives them a little kick to tell their kids to behave
Post: Best STR Mangement Company in Orlando

- Investor
- Leominster Ma
- Posts 305
- Votes 162
I shot you a message
Post: Orlando Area STR Single Family Home Under $500k

- Investor
- Leominster Ma
- Posts 305
- Votes 162
I own one in Story Cove. It was a 5 Bed for 680k I turned into a 6 bedroom. I agree with everyone else to get one in that price range you will have to look farther away and it may be outdated. This will hurt your bookings. I have people come to mine for a long weekend just to use the amenities. Are you under 500k because that's what you can qualify for or what you want to spend? If you can qualify higher I would suggest looking for that as you will find you will actually have a better return on investment
Post: What is the checklist for starting out in STR

- Investor
- Leominster Ma
- Posts 305
- Votes 162
Always here to help!
Remember there is also a lot you should be doing between getting it under agreement and going live. To maximize your profit you need to be able to go live as quick as possible with a great roperty. It should have anything you think is junky replaced or else you will just have guests talking about it or it breaking when a guest is there.
Post: What is the checklist for starting out in STR

- Investor
- Leominster Ma
- Posts 305
- Votes 162
ITs something Luke and Avery coined. You set the price very high while you finish your listing so you don't miss out on the boost you get for a new listing while finalizing everything that can only be
done after its live. It has to be done fast though.
Post: What is the checklist for starting out in STR

- Investor
- Leominster Ma
- Posts 305
- Votes 162
After purchase
Set up Price Labs
Set up hospitable
Ensure your cleaner you signed on earlier is still good and set them up with Ical
Visit the property to make any fixes needed. When I visited mine I realized a lot more was needed then I thought. Replace anything that isn't working GREAT
Ensure you have all linens and towels there (if the one you are buying was run by a rental company they will take all sheets and towels)
Set up your listing using the $4,000 method
Go Live
This is just a very high level breakdown
Post: Are condo-hotels good investments?

- Investor
- Leominster Ma
- Posts 305
- Votes 162
Condotells scare me. I am actually currently fighting in Orange Beach AL because they want to call the condo there a condotell. Here is my problems with a Condotel
1) The condo is non warrentable. That means I have to sell to another investor, cash, or some other portfolio loan. I will not be able to sell to any gov't backed loan, which severly limits my buyer pool
2) Its typically 30% down for a condotel and thet really destroys my COC return
3) If they run it for you that 25% off the top is going to destroy you profits. Its already hard in this market with a DSCR loan at 7% to make a good return
Post: Boston Short Term Rental

- Investor
- Leominster Ma
- Posts 305
- Votes 162
@Carolyn Fuller Thanks for that info. I did not know about this! Currently im investing out of state, but was going to start looking here for a BRRSTR
Post: How to structure a non-partnership deal

- Investor
- Leominster Ma
- Posts 305
- Votes 162
I am not a loan officer or lawyer but I have seen this before. You close on the home then have the deed changed after to reflect the second owner. I did it on my 2 family to get my wife on i before the 1031 exchange. Also be careful if you are the only one on it they can only "gift" you so much money. Ensure you talk to your loan officer and fully understand those loopholes