Still learning the ropes of all this but I’m anticipating a move to Dayton Ohio (I’m active duty Air Force so Wright Pat AFB).

If you purchased in the last few years I'm not sure that you'll have another equity after selling fees and misc costs to be able to move as much funds into the next property as you're anticipating.

Because all are trying to anticipate.

You can probably anticipate a 65% LTV max with this kind of lenders, and a lot more creative financing options. 

Out go-to title partner will provide this as a courtesy - otherwise anticipate costs of $125-250 plus recording fees (usually +/- $100). 

I was thinking, I could simply anticipate putting or than 20% down, like 40%, OR consider investing what would have been the rental downpayment in a REIT like Realty Income, ticker symbol “O”.

I use spreadsheets since they can easily be changed to anticipate changing conditions and "whatif" scenarios.

If you it takes 2 months to deploy, you are getting 10/12 of what you anticipated.

We chose a bad contractor to work with and ended up costing double what we anticipated and had to go back and re-do a lot of the work that was done as our contractor did not obtain necessary permits from the city.

We anticipated it needed $60,000 worth of work.