You may want to share you analysis with a few banks and/or property managers as they will typically weigh in on your assumptions if they are potentially interested in working with you. 

I'll be specifically looking to start in the Cincinnati, Ohio and lean towards targeting buy and hold single family and potentially multi family as well.Any advice is appreciated and I look forward to connecting. 

600+ credit score; income validation; we have potential tenants meet the existing tenants to make sure there is a good fit. 

If not for you and you prefer the traditional route, I would explore potential "up and coming" markets such as Acworth, Cartersville, and Douglasville, where the price-to-rent ratio is a little more favorable, and growth is apparent.

Their money, your labor is a potential disaster in the making; what if they don't like the install? 

Inherently the steps are the same as if you were purchasing with financing save potentially less closing costs and ability to close sooner (if needed).The terms of your offer (ie -contingencies, closing cost splits etc) will determine what is different. 

I am assuming that even if you strucutred it with a higher purchase price (85% of value) and pre-paid rent it would potentially still be frowned upon.

The market does offer lower priced investment opportunities and higher cashflow returns, with ongoing revitalization projects like the DORA boosting appreciation potential.

Vendors who partner with Costco pay for market exposure and referrals, which often adds to the final cost passed on to the customer.

The benefits of Kissimmee for a newbie is analyzing property potential is very easy - you will have a ton of carbon-copy comps to look at and the online estimators like Airdna can actually be pretty accurate.