Anything shady could become a habit, and potentially land you in trouble.  

If you have a lot of faith in the potential buyer I would consider whether it was worth pitching on being a 50% partner for $25k.

HOA fee will probably continue to increase, you never know when an expensive assessment is around the corner and there is some potential for a price crash as they are really overbuilding (imo).

Any advice, tips, or potential collaboration opportunities would be warmly welcomed.Thank you for taking the time to read my introduction.

I've got all of my ducks in a row (financing, agent, multiple potential deals).

You should be 100% fine as long as you do the proper research into your agents, pm's, etc...

If you want cash flow go to a market that has some potential, Killeen Texas. 

You don't buy a $350k property for 1,800 rent unless you want to capsize your portfolio or unless it is a holdover tenant and the property has a ton of appreciation potential.

Assuming both properties are/would be LTRs, these would be netted together on Schedule E, which would flow through to Schedule 1 and/or Form 8582.You'd also want to be aware of the potential for depreciation recapture when going to sell the property if you're not using a tax-deferred exchange.

Try looking into zillow/Redfin and see what your potential rents you can get near the neighborhood by filtering the bedrooms/bathrooms of the intentional property that you are planning to buy.