I would say that the section 8 experience has been overall the most rewarding on a deeper level.  

However, there are numerous ways to CREATE investments that have 15% or more cash flow AFTER repairs and allowance for cap ex.  

You both have to be on board or it doesn’t work, but if you work together and have a goal, then each step towards that goal feels more rewarding, even if it’s just saving $x more a month towards a future down payment.

there are numerous recent threads on BP by folks who bought something because it looked nice, or an agent recommended it, and they didn't see it themselves and approach it with any skepticism. 

Without more information, I wouldn't give much more than general advice which includes pros and cons.Risk, potential rewards, and skills make a difference. 

Search the BP for ADU appraisals to encounter numerous examples.

Home ownership is awesome and being a part of it is a truly rewarding feeling2.

You need to persuade people that selling to you is a better option than calling any of the other numerous solicitations they get in the mail every week or listing it with an RE agent. 

But if you can, then look to see about the cost versus reward of making it more renter friendly.If you just have a half bath, then adding a shower is critical unless you want to let these people use your shower upstairs. 

A LL may have previously rewarded her for not paying rent and you are considering doing the same.