I picked up about 20 units the other winter back, and burned through $200,000 in repairs quicker than you could write a check, and I have my own rehab crews that work full-time at this game.

Very few rentals close by (at least for now, in winter), but desirable location.We will do some updating no matter what:New laminate floor in kitchen/hallSiding needs replacing (have some insurance $ for that)Fresh paintNeeds new windows (maybe).Needs a bunch of concrete work (garage floor, driveway, stoop, walk to door).With those improvements we should be able to get at least $1000/mo.A room addition to add a large ensuite Bedroom/bath, and a laundry room to get the washer, dryer out of the garage, the bid came in at 59000 (This includes the siding).  

I don’t blame him as the winters in the UP are rough.

I've already spent some time on it, over the winter, and I'm done with it. 

I have an old building no central air but I do provide window AC units, I usually install them for them and take them for the winter time.

Not the best place for it, should have had them in interior walls, but it is not a show stopper, many homes do have that, hopefully they are insulated enough that they will not freeze in the winter.

One other note..... being near Hunter mountain gives you additional winter income so consider that as well!

PRO: you never have to worry about utilities being cut off in winter months potentially damaging your property.

I would add that the short-term rental cycle is seasonal here--there's a bit of a winter slump so be ready for that.

I have 11 units total in this complex, we already did a ton of fixes the last 3 months to the point where this winter should be smooth sailing besides if something with heating goes.