The difference between MKE and Chicagoland does not warrant the extra effort that comes with going remote.Everything gets so much more complicated as soon as you can't swing by your property after work.

Adding more details can help get better advice. 

If the home is 100 yrs old, I'm assuming it's a definite gut which is going to require new plumbing, electrical, heating, cosmetics.I spent about $140K reno on my multi family in the heights on NY ave and there were massive problems with it but it was a gut to 3 units & adding 2 bathrooms, 3 brand new kitchens 4 bathroom reno in total, all new flooring, sheetrock , insulation, framing, doors, electrical, plumbing, paint, parts of roof etc.

Perhaps I'm an old out of touch birdie, but if I made $292,000 a MONTH doing land contracts, I would focus all of my time and energy on that and adding to it.

Make sure it can handle the extra capacity before you get too far along.

That added a 12% expense bump- totally changed the vacancy dynamics.

Take the few extra hours it may take to originate the bank loan and divide it by the added finance charges and its normally more than most borrowers time is worth.

I do not see a need for extra cost or tech not all of your guests will appreciate (i.e. older generations).

Fortunately, even though I'm a newbie still in setup mode (working through renovations on a value added property) I'm already starting to recognize the right answers before reading the responses, thanks in big part to many of you.

I added 5 properties this year.