I am studying areas (zip code by zip code) with income levels above 45k and employment rate less than 3%.

I don't use a special lease or anything, and my guests are only staying days at a time. 

Your insights into how these smaller, specialized shops operate and the value one can bring by helping them modernize are incredibly valuable.

If that's not what your desired outcome is, do not get suckered into doing the FHA streamline refi.So at the end of the day, you have options, but if your goal is to buy another property, it's best to walk through all your options with a loan officer who specializes in working with investors and these exact scenarios, and map out a gameplan not only for your current property and next property, but getting to property 3,4,5 etc so that you don't get stuck on your journey.Hope that helps and best of luck!

Think about how can you make your property a no brainer when having to decide between an apartment and a home. 2-Contact homeowners who are not in your close proximity, so they do not feel threatened, and ask them what are they seeing in the market, and how are they are adjusting (most likely you are not the only one who is experiencing this). 3-  If you decide to work with a real estate agent, use one that works with rentals, and better yet, someone who specializes in property management as well, because they will help you weed out  bad applicants. 4- This last one I do not have experience with, but I would definitely try it if my rental was near a hospital: Partner with a company that finds housing for traveling nurses.

If you need assistance with the setup, my best friend is a lawyer who specializes in these matters and can help.

@Shawn Good, my understanding is Fox Lake allows STR but you have to get a special use permit and it's a 2 night minimum.

Regarding a refinance on a sub2, are there any special conditions or is it straight forward like a normal refinance?

Typically before the land is purchased, I advise buyers to perform all of the due diligence starting with the zoning and development code to know what is even possible within the confines of the existing zoning with the city/county.

I recommend finding an accountant who specializes in real estate taxation and tax planning.You may want to consider working with your accountant remotely to expand your options.I would also recommend looking for a accountant willing to work with you throughout the year.