Experienced managers can help evaluate potential investments by providing insights on rental demand, market rents, tenant preferences, and location-specific factors that affect leasing success.For example, rental properties need to be close to conveniences like major roads, shopping, and schools.

The other potential problem is the term of the proposed renter not sure exactly we are going to deal with their lease when it comes time to sell.  

Quote from @Reeti Peshawaria: Hi, I'm in the process of learning about short-term rental investments and analyzing potential markets, but I’ve hit a major roadblock: understanding local regulations.

We still see postive cash flowing deals here and lots of appreciation potential.

Cities like these offer untapped potential without the intense competition found in larger metros.3.

Post on local Facebook pages for contractor referrals, go to local REIAs, and ask your potential agents and PMs (even if not using a PM at first...you may at some point).There is only so much that service providers can do and many of them are far from "experts"; so, be prepared to be your own expert at being willing to figure stuff out as you move forward.

Residential subdivisions, while potentially less complex, can be hit-or-miss depending on local housing trends and the cost of infrastructure development. 

Small upgrades or re-leasing to market rents could boost your cash flow and provide additional funds for your San Diego purchase.If you'd like, I can connect you with a lender or help you explore potential properties in your preferred areas to see what’s realistic within your budget.

Sounds like a good plan, should have plenty of options available.I would be cognizant of any group you talk with on two areas, the location of the property including any potential concerns of it being 'rural', as well as the minimum purchase price and/or minimum loan amounts.

I have a hard money lender at 10%, who will amortize at 30 years, with 5 year balloon so a potential loan of $200k is in the works.