So anyway the new home is everything we always wanted and a lot more like bigger mortgage, more taxes, bigger utility bills, a lot more upkeep cost, bigger lifestyle and on it goes.

Hello BP Community,Sorry if this questions seems a little simplistic,  I'm looking to buy a multifamily in the Worcester market and was wondering,  wouldn't I need to find a PM that I will use for the eventual purchase, and use their knowledge to leverage my due diligence on estimating cost/expense for the monthly upkeep. 

talk to Peak Asset Lending in KC  @Alexander Felice  banks generally wont fool with stuff this low unless you have existing relationships with them.. the cost and risk of having a default far out weight what a bank can make on a 15 to 20k mortgage.but i have seen small local commerial banks do these for local citizens that own 10 to 50 homes and its their cottage industry so to speak

That event is heavily weighted to seller carryback investing rather than NPL investing. 

I’d just like to off set the payment/upkeep initially. 

Don’t give up. Keep

(Verbal agreements don't carry a lot of weight with real estate, so you'd likely prevail either way, but do you want the tenant's free "tenant's rights lawyer" to drag you through the mud for months, or weeks?)

I think the biggest concern I have is that you are calculating your "cash flow" without factoring in ALL you expenses.Lets say you are "losing" $1000/month....but it would cost you $1200 to live somewhere else.... so you aren't really losing that full $1000/month....since you have tax benefits, equity, possible appreciation etc etc.......but do you have the cash to deal with that "loss" and be able to afford the expense that will come up..... the upkeep, repairs, rehabs, turnover etc etc.....other expenses WILL come up....not IF but WHEN....When you are accepting short term "loss", you are counting on a long term payoff, often via appreciation....plus you have to have deeper pockets to weather that loss for extended periods

It took hours to set all those checklists up but for $10/month, its worth its weight in gold because I don't have a single doubt that my housekeeper knows what to do because its on the checklist. 

Even just a weight and breed limit would be a start.