Indy is actually a rather popular city for guests looking to staying at a STR.

Depending on the location STR is going to make the most money because condo rentals are an attractive option due to the amenities.

When I try to analyze a deal, I feel like there are so many steps within each step that make it more difficult to actually figure out how to do it.

I think some of the answer lies in your personal goals and in the amount of money you have available to you.

Or lastly, save money for new family home, take some equity out to put towards our down payment towards our family home, and then rent out the house?

The idea that you can build wealth without putting any money into it is a recipe for disaster and the sales pitch of gurus trying to steal your money.

I actually ended up going with a different software, so I probably won't be much help here!

You might end up paying a few hundred dollars a year to the state you set it up in, and the state you are actually doing business in. 

we have 7 new builds breaking ground in July all are for clients that we build at a discount for and they resell which makes the economics even more favorable for them but for our side of things I haven't looked at private money just through all cash partnerships. that's in columbus ohio 

Toilet backups are really a myth for the most part that every potential landlord worries about but things like that are actually extremely rare.