We have started to think about selling the property and using the proceeds to buy another home in a more desirable area where we believe market and rent appreciation has greater potential for growth.

IMHO, starting at $150 was way generous, and I'd stick to that number.NOTE:  If they actually couldn't stay in the property, they could claim that against their renter's insurance--that's one of the reasons it's there, and why we require it on every rental.  

I’ll start with one that was only doable under the special circumstances of the late 1970s early 80s.  

However, it is hard to gauge the rental potential so many years into the future with new construction SFH and apartments being built in the next few years.I’m worried about the HOA, the rental potential, whether I should keep saving and buy a SFH, or if I should just take the plunge and start building equity.

We are starting to see panic selling and homeowners trying to find alternatives to selling.

I have 2 rentals (1 already in an llc and 1 being put in now), I am at the point of starting to look at getting a 3rd rental and have always wondered what loan approval will look like with my assets now segmented and if I would apply for the loan as the LLC.

Fico Scores can drop fast when a person starts to open and take out multiple LOC's and mortgages which is considered "Excessive tradelines" based on your DTI.Helocs are great for quick renovations or repairs and should be used and paid off or down quickly.

I started out with a flip house and am currently focusing on long-term rentals.

Does anyone know if I am able to start an LLC and run short term rentals?

At a lower price point I will say that you start to see lower quality applicants.