to supplement my pensions and 403b.

Some of these are pretty specific to single-family and small multifamily in western Pennsylvania, so I'm getting some of your "cold/temperate climate" supplement.- Continually monitor/check brick veneer for repointing, sagging.- Check chimneys for cracks every two years in elderly properties.- Annually trim back tree branches extending near or over roof.- Perform radon test every 5 years.- Perform sewage line inspection every five years, especially with old, established trees in obvious vicinity to sewer line, maple root systems are typically shallow and extensive (<5 feet)/oaks go deeper and never stop growing even if the tree branches keeps getting trimmed back (>5 feet).- Monitor typical icicle build-up, watching for insulation/roofing degradation.- Glyphosate weedkiller application 2x yearly, early spring, midsummer in problem areas.- Check window trim for wood rot (I have a constant bone to pick with window replacement companies that offer window wrapping for older homes, completely hiding existing trim as it degrades further and lets in more cold air!)

What supplemental materials do you typically ask for? 

Also getting your brokers license is a good way to supplement your wholesaling income.

You want to stay with the market, no reason to charge less, it will have no effect on whether tenants stay or go, tenants are prepared to pay market rent, charging below market is only costing you money to supplement your tenants rent....charity.

In either scenario you are going to need PM at some point so I would focus on clearly defining your short term and long term goals; are you trying to build a portfolio so you can live off the income, purchase a couple properties for supplemental income, scale a large RE business?

I'm going to list off some of the lowest hanging fruit from that perspective below:Attic/ceiling space often can be helped immensely by blowing in additional cellulose insulationWindows and all wall terminations should be examined and caulked/filled with expanding foam insulationWalls can often be supplemented with additional insulationRim joists, basement walls Look into selectively upgrading your main appliances (water heater, air conditioning, furnace) with high efficiency unitsOld fridges use a lot of electricity - you might take a look at what you have there and consider upgradingSome utilities have programs to offer rebates/incentives for upgrading much of the above so I'd look into that if I were you!

You have reserves put aside which is excellent, the VA is no money down, and the income produced by the other 3 units will give you supplemental income while you establish yourself. 

My condos have doubled in appraised value, and in addition they now net a combined 41K per year which is, for me, precious supplemental income.

I'm only looking at real estate investing as a way to supplement my retirement in 10 years as apposed to putting more money into a 401K.