Regarding financing (and sight distance approval), maybe having your architect make up a small model with people and cars to help sell the project to the bank.This could be costly and of course there's no way to measure the effectiveness on their decision. 

I am trying to figure out if people generally run these are sole proprietorships or through an LLC.

Very knowledgeable in very forum and super friendly people.

There's a number of people that teach/coach how to start and run a STR company...Tony and Sara RobinsonMicheal Sjogren Rob AbasoloMicheal ElefanteAnd others depending on what fits your goals. 

I had already factored in self management...I’m just wondering how people do just continuing STR over the winter months.

@Rajin SainiReach out to private lenders here on BPHappy to take a look at some of your dealsWhat we find to work the best is honestly not sell anyone but just tell people what you doYou fix and flip a few homes per month using private and hard money

I am looking to connect with people who are doing out of state investing.

I aim to utilize other people's money to invest wisely in buy-and-hold multifamily properties.

Would I be required to have a liscence in order to engage in this type of transactional lending?

Totally a viable option but keep in mind the documentation of the process and making sure that YOUR material participation does not exceed anyone else in the home - for example, your cleaners or maintenance people.