My dad used to manage other people's properties but eventually quit because the money wasn't worth it and he always ended up prioritizing their properties so as not to get any hassle from them.Another way to approach this might be to go all in on one project yourself and see how far that money gets you. 

What factors should I prioritize when choosing the best approach for my future success in real estate? 

Unfortunately experience means you've made some costly mistakes :-) So, to avoid those costly mistakes, when I take on a new approach in investing, I buddy up with someone that already has experience doing them.

Since they are responsible for maintaining the relationship with you after the transaction closes, this approach adds an extra layer of confidence and security to your investment.If you can't find an investor agent that you like or trust that is also a Property Manager or works under a brokerage that has a Property Management Division, I would ask the agent if they recommend a Property Management Company.

The military brings a lot of folks out here with a healthy BAH to rent but you usually can find 2 bedrooms hear for around 2000-2500 (depending on area). 

Rents can’t realistically continue to appreciate at the rate they were if we are to maintain a healthy housing sector.

In addition our healthy balance sheet allows us to pre buy mortgages down to as low 3.75% for our buyers, most builders can not qualify to do this.

It’s a lot to keep track of, especially when researching multiple markets.Would greatly appreciate any advice/insights from experienced investors who've navigated these challenges :- How do you approach understanding and evaluating short-term rental regulations when considering a new market?

This approach avoids downtime and lets you start earning right away.Future Bookings:Taking over bookings can get tricky since Airbnb doesn’t allow direct transfers between accounts.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.