Hey there @Colin Williams, So if you are looking for a great way to logically price your Vacation Rental / Airbnb you can check out AirDNA, my company Hoasty is a customer.

They weren’t all that familiar with my local customs (taxes etc) so there were some hiccups along the way .

That will allow you to get a background knowledge of the real estate laws and customs in your area.

I don’t plan on insuring it for my mortgage value but when USAA is telling me $2100 for an outsourced wind/hail I’m just trying to find an insurance company that takes care of their customers like USAA but I don’t have to pay an arm and leg for either for wind and hail.

Unless you are going ultra high end and custom I never saw a reason to buy those things anywhere else.

Most of our properties are 1-4 units with a smattering of commercial as well almost entirely in South and West Sides (no suburbs).I don't really care about the size of the bank but, ideally, we would find a bank that has:- Great customer service- Competitive fees- Highly functional online platform (and services that can help reduce overhead, like remote check deposit)- A willingness to at least entertain lending to an operation like ours (long term financing and potentially some operating lines)Any ideas/intro's would be greatly appreciated!

Remember, it's basically a little hotel, so expect to provide customer service, cleanings, WiFi, etc. to your guests which you will be paying for.Here is a quick BP article that I wrote that goes over some of the pro/cons of owning an STR: https://www.biggerpockets.com/member-blogs/10042-vacationhouse4free/64744-5-reasons-vacation-rentals-are-a-bad-ideaso-do-it-anywayBest of luck!

I have done everything from electrical, framing, drywall including mudding, plumbing, hardwood flooring, tile flooring and custom showers, decks, tractor work and roofing.

I do it all the time for customers.

Luckily there's a custom answer out there for just about everyone.