That sounds like an ideal situation versus doing a full fix and flip for your first deal. 

Some people don't have financial situation, nor have the bookkeeping to track or maintain it.Again, I personally find it very stressful just thinking about living that way for the life of the loan keeping the lowest daily balance possible. 

It sounds like you’re in a tricky situation!

Depending on the tenant and what their financial situation is, you might also be better off giving them a 60 day notice and just telling them that you're planning to move into the property and do some updating. 30 days is usually too short for someone to have to move on, 60 days is plenty of notice for them to be able to pack and find another place.

Sounds like you have some great tenants and I wouldn't worry too much about this situation. 

MTR is less hands-on compared to STR so that would help with the guest follow up situation. 

It seems to be tracking status of the areas, which if there's still momentum in those areas could help situate someone for future growth. 

You're just fishing for situations to get a deal.

For your situation it's hard to say, but look at both options and see which one fits your investing strategy and risk profile more!

I want to help but also don't want him to do something that jeopardizes his income so its a tough situation.