They would like to keep the timeshare as they are reaching a point where they want to take more frequent vacations and it would help cover the cost of those trips.

The way you are breaking it down is very spreadsheet-friendly in terms of what would work in a best-case scenario, but landlording for five room hackers is not easy and the rent is not easy to collect in all cases.

I'm particularly passionate about Fix and flips and Airbnb.Outside of real estate, I enjoy spending the valuable moments with family, friends and building fresh water fish tank aquariums as a hobby.Excited to learn and connect with you all!

There are other avenues to review but I agree past rental history is important (disclosure I have 15+ doors right now)If you feel bad for them then rent to them.My point is its corporate america and you are blaming the wrong person - you are blaming the corporation but you should be blaming the politicians who create an environment that is tenant friendly and sue happy. 

Software is very user friendly, reports are easy to understand, owner and tenant portals are also user-friendly.  

If you have any tips on reaching more people and building a pipeline while staying budget-friendly, I’m all ears.Looking forward to learning from this community, sharing what I know, and getting back into the real estate game full force.

Find a local investor-friendly realtor in your area who can give you an overview and assist you as you start to get to work.

Your spouse, partner, friends, or family are not on board with real estate investing.

(Mass Govt should be giving experienced landlords (5 years operating with at least one unit at profit as a buy and hold) zero down loans to house these people (in areas they currently live in--so they can stay close to friends and family), and free money to fix up the Brockton type area homes to modern standards inside. 

@Teahjsia Frazier - If you're targeting a BRRRR for your next deal I would consider using a combination of your money, private money (friends and family), as well as hard money for the purchase and rehab.