Good question - I've been house hacking on this property so your question made me do some math.Currently I rent a one bedroom studio for $1,100 which covers the $899 mortgage but not other expenses.

For those who’ve used it, what strategies or sources have worked best for you when covering the difference between your loan and the total project cost?

Of course, with all things, the answers to all these matters will depend on the circumstances.California tends to have more laws on the books and requirements and restrictions that it can be a good idea to form a CA LLC for out of state property so that you as a CA resident are covered, and to try to have your contracts fall under the purview of CA courts.

There are short-term rental management companies that can help with that.One that I work with in Michigan covers the entire state and can advise on local short-term rental regulations or regulations that may be on the way, they can give you an analysis of the demand for short-term rentals in that area, nightly rates in that area, monthly occupancy percentage, and projected monthly income.They also let you choose the level of service you would like from them from full service to minimal.To your success!

Since you won't be able to recognize it as a valid rental if you're charging under market rent and you also expect to be covering any house expenses that are outside of her budget, this seems the best choice. 

The left over would cover the difference in monthly payment for about 2 years.

Hey Natalie if you're set on holding onto the property I have a great property manager I use for my STR's that also will cover MTR and LTR's.

If s/he'd been putting aside reserves, the repair would have been covered by funds already in the bank. 

Now I straight up said there has to be some kind of contract and price and they did cover it with me (I don't know if they normally do that or only did it because I asked), however the price is $15k-40K or more.For me this is a major red flag and irresponsible.

The plumber insists that this is definitely a city issue, but I’d like to hear from others who have dealt with similar situations.Would the city reimburse or help cover part of the expenses for the secondary cleanout?