All Forum Posts by: Sushil Gupta

Hi everyone,

I own a few rental properties that are currently under my personal name. I read through BiggerPockets article on LLCs (link) and few other articles, but they do not help enough. Therefore reaching out to community directly 

From the article, I understand that:

• LLCs provide a liability shield if set up and maintained correctly
• There are some financing and due-on-sale clause risks
• One LLC per property = better risk isolation, but more cost/complexity
• Grouping properties under one LLC = simpler and cheaper, but more exposure

I’d love your perspective on a few questions:

1. Does it make practical sense to have LLC?
2. Have you moved properties from personal name to an LLC? If so, how did that process go—especially with your lender?
3. Do you personally structure your portfolio as one LLC per property or combine multiple under one?
4. Any regrets or lessons learned?
5. How much value do you see in this versus just having great insurance + umbrella policy?

Context: These are long-term rentals, not flips. I manage them myself.

Thanks in advance! Appreciate any guidance or experience you can share.

@Peter W. 

@Peter W. Thank you. 

All tier-1 cities have high priced homes and will be cash flow negative. Will bearing that -ve cash flow and 4%ish ROI, be overshadowed by the appreciation say in 10 years?

I’m exploring real estate investment opportunities and want to focus on markets with the highest potential for capital appreciation over the next 10 years. I’ve noticed that some Northeast and Midwest cities have recently led in price growth, but I’m curious to hear from experienced investors: • Which U.S. markets do you believe will deliver the strongest capital appreciation in the next decade? • Are there specific cities or regions you’re bullish on, and why? • What factors are most important to consider when targeting appreciation-focused investments? Any insights, data, or personal experiences are greatly appreciated! Thanks in advance!

Quote from @Renee Krystek:

Hey Sushil,

I agree with those above, CA is tough! Though our design company has had quite a handful of new STR owners coming in from Wine Country and Coachella so I do know it is possible.

If you haven’t already, definitely connect with a local agent who specializes in STRs someone who knows both the regulatory map and what guests are booking.

And best of luck!

 Makes sense, thank you, Renee

thank you all, which would be good places to invest in CA for STRs? Given this is gonna be my first STR, I want to be somewhat more involved in the beginning.

Hi everyone,

I’m exploring opportunities to invest in a short-term rental property in Santa Rosa, CA and would love to hear from folks with experience in the market. Specifically, I’m looking to understand:

• What's the current demand and overall sentiment in your STR market?
• Is Santa Rosa STR friendly? How hard or easy would it be to secure STR license.
• Are there any recent or upcoming regulatory changes (Airbnb/STR laws) I should be aware of?
• What areas are still investor-friendly for STRs in terms of returns and local policies?

I’d also appreciate any recommendations for agents or brokers who specialize in STRs — folks who understand both the numbers and the local regulatory landscape.

Feel free to DM me or drop your thoughts here — thanks in advance for sharing your experience!

Also this will be my first STR - in Santa Rosa or anywhere else, and any additional guidance will be very much appreciated.

Thanks!

I currently own a few investment properties and am looking to finance additional ones. Many banks, like BOFA and Citi, have limits on the number of financed properties they support. I’d love to hear from other investors—how have you secured financing for new properties after reaching these limits? And are those financing options gonna be more expensive than conventional mortgage from a bank? 

Quote from @Nick N.:

I have some knowledge of the Jax Beach market and would be happy to connect to discuss your investment ideas.  PM if you'd like to connect

Will do. Thanks. 

Hello, 

I am looking at investing in Shearwater community by Lennar in Jacksonville. Currently it will not be positive cash flow. 

Need inputs from someone in that area:

1. How are rental increases every year in that area? 

2. Given this is newish area, how hard it would be to rent and its vacancy rate? 

3. Given market in the area, coupled with lot of growth, what is the potential for capital appreciation on this property say 5 years down the line. 

4. Can I attract high quality renters for this property? 

5. If this is not the place, then what other places in Jacksonville should I be looking for? 

My goals are 1. to make this property cash flow positive in few years, 2. to earn capital appreciation over the period of 7-10 years. 

Thanks, 

Sushil