Your friends/business partners should be able to drive by the property at least once a month to check it from the curb and make sure basic maintenance is being handled (the lawn mowed, place isn't looking trashy, etc).  

We are wanting to split into 3, 15 acre lots to not be considered a major subdivision (it starts to get crazy with roads, curbs, utilities, etc), but as a minor subdivision (4 parcels), we will be able to bypass those expensive improvements. 

I had a 50% grant from the city's curb appeal program a couple of years ago for new windows, siding, some roofing, fire escape, etc.  

Several times there was no ad, no sign and people would stop because there was a bunch of trash on the curb. 

Make sure you have curb appeal. 

It has curb appeal, but it is definitely the worst house in the neighborhood by far because of the trash.  

I took down a tree in the back yard which really opened it up as well as some dead trees in the front to help the curb appeal - I truly think this added value.

While in between occupancy I would try to update each side accordingly as with the exterior curb appeal.

If you do something with the stairs it will bring more attention to the entrance and up the curb appeal. 

Bggest hurdle is curbing wasteful spending and getting family in line with your goals.