Let's say the city cites them for violations and they rack up penalties and fines. 

On the other hand, if you write something into the lease that you agree upon, it should be fine, but that may turn off many prospects IMO.

My humble advice to anyone attempting to do creative finance is:Creative finance is for experienced investors who have access to capital if anything goes wrong.Learn the lawsDon't use a contract "off the internet", laws vary by state and are also regulated on a federal levelLearn the financing techniques correctlyDon’t skip parts of the processDon’t ever do a “kitchen table” closingUse the proper deedAn attorney can help you with the legal work, but the rest you are on your ownYour guru will not bail you out“Investing” in someone else’s deal by providing a small 2nd loan so the “investor” can pay for “cash to the seller” and for “closing costs” so he can do the deal is a very bad planKnow what problems can ariseLearn the responses and solutions to problems before they are neededKnow everything there is to know about Title and what that meansKnow who a "protected class" individual isLearn the "back doors"Learn human natureUnderstand timelinesUnderstand regulation enforcement (some of these "mistakes" have a 10 year statue of limitations ( they can charge you 10 years AFTER you do the transaction) and carry hefty fines and possible imprisonmentThe court doesn't accept "I didn't know" for an answer"Know that the source of the lead plays a serious role in some states and federallyKnow how much of a "profit" pushes the boundaries to invite an investigationYou can be sued by the seller if you don’t do things correctlyYou are automatically at fault if an investigator or attorney or regulator gets involved.

I’m 37 and I’m wanting to do real estate full time eventually(if it takes 5-10 years, that’s fine). 

There is a fine line between offering a well rounded service and leaving too much in the home.I love the business and glad to be a Superhost but this has been my experience.  

I actually ended up going through a big career change, and attended a 6-month bootcamp to learn Software Development after 7 years cooking professionally in fine-dining kitchens. 

Also, if the sponsor is new, I am fine with less skin in the game as long as it is significant to their net worth.

I've got a long term tenant lined up & the unit is a non smoking unit, which the applicant is aware & fine with for indoor.

If I go the multi-unit route I would put myself in debt for a bit, which is fine for long term investment.

But if it's coming at the cost of your health or something else important than time with your family then it's perfectly fine to step back when you need to.I think this goes without saying.