Minimum rentals allowed for a year, and maximum too.What are some typical loop holes I can look for?

An attorney or some monetary payment maybe needed to get the occupant out.

Starting down the rabbit hole of investing is great, but there is nearly an infinite supply of information and insights that can and will prove useful to you, so always look to learn more. 

They look great and allow much more light into the hallways.Jen tackled sanding and painting the hall ways hall way 2 is complete with hallway 1 not far behind, all that's left is stair treads.Bathroom in Apt 22 came together with installation of the vanity and fixtures.Some odds and ends also got completed, door hardware, exterior electrical patching some holes and paint and the lawn guy found the rest of the sidewalkThat's it for Week 7 so far we are on track and on budget, stay tuned....

Unfortunately, that's actually as close as the wrong lawsuit happy person stepping in a hole on your property and twisting their ankle- but an LLC would offer your personal assets {and other investments} safe)If it's just yourself, taxes are not so complicated with a SMLLC (single member LLC) so that shouldn't be a huge reason not to use an LLC(s), as the protection benefits offset/outweigh the small steps during tax time.For future note, it's simply a matter of attaching Schedule C form to your Individual Income Tax Return (IRS Form 1040) and showing a total profit or loss as part of your total income that's being reported.

Feel free to reach out just to network, but looking for help on the following items/questions: Any obvious holes in my search criteria?

There was a hole in the shower with mold growing from it, there’s a hole in the basement laundry room floor. 

If you burn a section of the counter, or put a hole in the wall, you will be charged X as we have to paint the whole wall/replace the whole counter etc....make it part of your lease moving forward.  

Just a quick 'protection' in what I mean- if you currently hold these three properties in your personal name, do not have an umbrella  policy, and someone falls in a hole on one of the properties and breaks their ankle - it's you personally and your personal assets on the line. 

My girlfriend is from Chester, MA (smack in the heart of the Berkshires, if you will) and the local facebook group is the most liveliest watering hole I've seen in many a moons.