@An Duong it's really up to you whether it's a good enough deal for you to agree to that.I will say, besides the two years of below-market rent, you should also factor the cost of an eviction into your thinking.It may not end with an eviction, and if it doesn't then you'll have saved some money, but I would go into it with the assumption you'll have to do one since I think there's a non-negligible chance of that.In a negotiation, sometimes it can be helpful to try to figure out the other person's motivations and find other ways to meet it.For example, if he's worried about being able to afford market rent, then if it's $200 below market a month, and you don't want to tie the unit up for a second year, maybe you offer to pay $2400 more at closing and only have him there for one year.If he really likes the area, maybe you find him an apartment in the area and offer to pay his security deposit, a moving company, and X months of rent to get him started.

The "detached apartment" model remains a mystery to most, as the majority of the mobile home parks in the U.S. do not agree with that model -- but you are correct that in some parts of the U.S. the low lot rent (typically around $100 per month or less) makes the straight land rent business not compelling. 

This floor drain is tied into my tenants kitchen sink (kitchen sink does not seem to be clogged according to my tenant).

You need/want 5 years of roof life remaining - and the same for AC/Heat.

You could buy, reno, and flip or refi to long term financing (BRRRR).I do not recommend tieing it up as a long term hold. 

I tend to get tied up with working on getting everything working and neglect the personal contact.

Selling way below tax assessment could be a good signal, but don't count on the tax man to do your due diligence for you :)Honestly I'm not even worried about value add, the property is, from an aesthetic perspective, in phenomenal shape, and anything on the internal/infrastructural side of things does certainly remain to be seen.

The property's sewer/water/trash bill comes in Quarterly from the borough it's in and the account is tied to the house. 

You can expect approximately 50% of rent income set aside for expenses, then you pay the mortgage and interest, then anything remaining is your cash flow.If you can break even using the proper cash flow calculation, then I might consider a property based on appreciation.

Cash out refi's are generally 70%-75% LTV (loan to value) of the ARV, which means that the lender could give you $38.5k - $41.25k.The lender will use that money to pay off the existing loan of $36k and cut you a check for the remaining amount.This would only leave you with $2.5k - $5.25k cash after the $36k loan is paid off.