However, i need good funding partners to push ahead in order to take calculated risks.  

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).

EDUCATE YOURSELF - yes, it will take time, but will lead to a selection that better meets your expectations & avoids potentially costly surprises!

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.

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).

Most of the OOS markets investors target do not have much appreciation potential, are lower end properties that will have ongoing issues and will not give the OP the opportunity to self manage his units to gain true real estate experience and understanding.

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

If this coach is in your market and knows the key players in the market, has used various property managers and can tell you the good ones, knows the loan brokers, knows the risks of investing on this side of town versus that, knows the tenant base for your area and what they are wanting from their apartments and what they can afford, than I would say a coach (maybe not the one you are interviewing) is worth it.  

What else can i ask just to prevent potential issues with a tenant.