I have a handy man that gets called on for all of the odds and ends that I can't get to. 

I know a lot of people would look at this as a little odd, however, I am looking to get my feet wet and figured if I find a good deal, finance it with hard money, take a loss for a hand full of years (due to typical high interest rates with hard money) and then get a traditional loan later, would you do it? 

Managing an STR is a lot of work, odd hours, and able to show hospitality to everyone while holding fast to boundaries and weeding out the party groups.

This seems a bit odd UNLESS you were priced on the wrong program to begin with....

Considering most businesses fail in the USA odds are better that you'll fail than succeed.Collection.

Anything odd regarding inspections that I should be mentally prepared for?

You can help your odds by talking to a few realtors before choosing the one you think is correct for you.

I found a house with an odd layout - it's a 5/3, but one bed/bath can only be accessed through another bedroom, or from outside through separate entrance.I'm looking at separating the house to create a 4/2 traditional rental and an attached 1/1 Airbnb.

Odd that he's approached you, for you to do all the work up front but he wants equity?

That's odd.