I ended up going with a STR for the first one because the cash flow was that much better.It made it a better deal for us because we can still use it occasionally when we travel to the area but still make plenty of money to cash flow more than that of buying a triplex or a quadplex.In the end it really comes down to what are your goals for the first property.

People are traveling now so it will be a seasonal summer but the market will still be hot.

Don't overlook mileage and travel expenses.Each LLC might also file a NY state tax return.

We are open to long term real estate investing, but we would need to research more and become confident in a specific area prior to doing so.

Make sure you've researched the area well enough to come off confident and knowledgeable to the owner. 

Retroactive tax policy is terrible and shakes confidence in the system.

I don't want to ask that question, because I don't think it has an answer, and I think even spoon feeding someone an answer, they still are unlikely to have success, as they haven't done the requisite homework to evaluate and make best use of even a great answer.I'm a travel nurse, so I am quite rarely ever home.

Jeff Stoller is one person I can recommend with 100% confidence.  

The way i figure it, these locations have good opportunities in terms of both cashflow and appreciation, are far enough from NYC to be smart investments, but close enough that I can travel there within a few hours by car if ever the need should arise.  

I'm looking into a property right on the Oconto River, 30 minutes north of Green Bay (I'd assume Packers games would bring in some STR activity as well).There are a handful of STR's in this small town, and the state regulations seem to favor STR's to promote tourism and travel.