This has worked out great since we can also apply our knowledge of the vacation rental industry and what works best once we are booking the home (themed bedrooms, game room, best bedding configuration and much more).

I switched many years back to a refundable security deposit.Insurance seemed like they had no skin in the game.

EM and due diligence sure thats part of the game  but actually closing we would not do that for what is basically market price.  

You appear to be banking on appreciation, which can be a dangerous game and not something that helps a long term buy and hold investor (appreciation does not help cash flow).For me, without now much information, I would not be interested in the property for anything more than $200k, and that would assume that rents are at market rate and the property is in pretty good condition with little deferred maintenance.

Brand new wanna be investor in Orlando FL that has been reading books and game planning with girlfriend partner.  

A college student looking to get in the game early I'm saving up to get my first rental but I want to give private money a shot to get it done quicker, but then again with this market I also feel I should wait.

I’ve been in the game for nine years and I believe real estate is my end game.

add a real estate license to your game and go get into that community  tons of agents lenders inspectors  title and escrow etc. plus it will help you increase your earnings doing what your already doing.

So I’m wondering, as well as my initial work getting the deal should I have more skin in the game.?

I checked my credit score a few months later and it had gone from 750 to 620.....they don't feel you're a good risk if you are debt free I guess.....It's all a big con game anyway.On the other hand, $215 a month is not a huge amount in the game you're playing anyway.....you can make it up somewhere..