I am considering offering him $1.8m with a low (or no) down payment and seller financing at a low interest rate so I can at least break even on cash flow after getting rent closer to market value and with upside potential as a MTR and strong  appreciation opportunity.

I just maybe have been lucky but the age does not scare me if the price is right and the inspection comes back clean. 

For this deal to work under those conditions, the purchase price would need to be closer to $179k.With your original assumptions 249k, the deal is marginally acceptable but not great, given the negative cash flow in the early years.

Know your market cap rate and you can quickly determine whether property is worth a closer look. 

Quote from @Yaroslav Shtogun: Good morning,Some updates, we did home inspection and the house is not good condition since it was built in 1950 and was not maintained well.

All contact, maintenance, inspection, lease, anything is handled in a queue....not a call.

.- PM is contractually obligated to perform annual maintenance/inspection to keep property in top shape. - PM provides a cash based accounting report every month, for every unit under management, that clearly labels all rent, all expenses, including management fees, and the net directly ties to the amount of money deposited into my bank account.- PM is a licensed handyman, or has them on staff, and takes care of most unit turn work at a reasonable rate. - PM has no breakup/termination fee- PM does not take project management fees, except on large or complicated CapEx projects exceeding $5,000. 

Know this (found on every inspection website):  You should be concerned about cracks in your home if they are large, appear suddenly, or are located in certain areas.

If the house has a septic system, especially if it's an older one, it's worth the investment to have a septic inspection done.This concern is particularly relevant for those planning to buy and hold the property rather than simply fix and sell it.

Closer to 500k the better.