I have an MBA degree, and I can swing a hammer.

Yards that haven't been watered or cared for since install. 

Buy box: Location: Approx. 30 min drive to Boston Heights, for workNeighborhoods: Decent walkability score - not far from shops/restaurants/trendy neighborhoodsIdeal tenants: Close to hospitals/universities/schools for professionals/students/familiesBudget: $175-250K - Buying w/conventional loan, 5% down/ approx 20K reno.Property type: MFH 2-4 units - preferably side-by-side, with a yard we can fence for our dogUnits: 3+/1+ - better if 1.5/2 bath per unitTimeline: Plan to live there for 2 years, but possibly only 1 year if we find another investment opportunityGoal: Focus on appreciation - would like to see cash flow in year 2-3 (the year we move out), including overhead (Vacancies, Maintenance, Utilities) and budgeting in PM if eventually we don't manage ourselvesValue add: Opportunity for some forced appreciation, but not a full reno - cosmetic upgrades and updating kitchens/baths while we live in one unit.

She doesn't want him to leave because he helps to take care of everything that his son never would, like picking the kids up from school, fixing things around the house, mowing the yard, and taking out the trash.

Just swinging for the fences herePortfolio Loan or Blanket Loan: Use the combined equity of both properties to secure a new loan.

Maybe even allow for a small kitchenette for full privacy, although it would be attached to the house with a connecting door.The yard has enough room to allow for it.

They acknowledged that if the tenant wants it adjusted to exclude that area then we'll revise, but they want to charge for the entire space...to them it is an integral component to leasing the yard since the City mandates screening landscape.

They don't swing for the fences every time.

Maybe a yard maintenance (gardening, snow removal, lawn maintenance, etc) service. 

It's a large yard that overlooks trees and such.