If I didn't know you or your husband from any Dick, Jane or Mary, and you refused to show a proof of funds or Pre-Approval... and refused go meet with them to ensure safety I would wager its not safe for the agent. 

I'd wager the latter may be costlier. 

On paper the guy spending 30K to buy a house that rents for $750 is beating me, but I would wager at the end of a 5 year period, we'd come out pretty close.

Rochester has some very good streets and some very bad ones, in many of the neighborhoods where you can make good cash flow.Right off the bat the rents seem a little low, along with the price, so I'd wager you'd be looking at a fair bit of deferred maintenance.Have you walked through the properties yet?

While I don't think there's a "crash coming" in 2 months, 12 months, or in any defined period of time...well...I'd wager there's some pull-back over the next 14 years. 

@Gannon Nikolich You should start putting together a package of information to give to lenders; including your new leases, personal financials, property information (taxes, insurance, recent repairs), etc.Without knowing anything about the property, I'd wager that this is a deal for a local/regional bank. 

I would wager it is only for SFR so you would need to get a roommate to get the house hacking part of that going.

Without seeing the house, I can basically wager that you're perfectly fine if those are the only "issues" that came up.Too much Holmes on Homes has convinced people that when there's a pin hole leak in a pipe you spend $50,000 remodeling the kitchen.

Any service or advertising contracts: (Trash, extermination, maintenance, management, commission agreements, union agreements, vending, billboard, pay telephone, etc. and any instrument or contract to be assumed by Purchaser) Copies of all recent appraisals, engineering reports, environmental reports Survey (as-built), legal description, architectural and engineering plans and specifications Payroll register: List of employees including name, position, wage rate, and entitled benefits Business license Physical inventory of furniture, fixtures, and equipment, and supplies.

Given my familiarity with Winchester, I'd wager that this is C-class asset, which reinforces my suggestion not to manage from a distance.Although there have been significant issues, the tenant isn't entitled to withhold rent or dictate terms to you.