Roofing, painting, major tree maintenance, concrete repairs (sidewalks, driveways, building spalling) and much more.

The bumper to bumper traffic was constant, and the sidewalks, restaurants and shops were crowded  … but was it day trippers from nearby cities?  

Sidewalk costs,j. 

We found a piece of land that was similar size to yours in an area that was ripe for townhome development but was rectangular in shape.After talking to a consultant we found that the land was not wide enough to accommodate townhomes on both sides of the rectangular land as we had to account for roads and sidewalks in between the homes and those had to be a specific size based on city rules.The seller believed that we could fit about 90 townhomes on the almost 6-acre parcel, however, we could fit only 45 to 50 townhomes as the land was not wide enough.

Plus worrying about a kid zipping down the sidewalk from behind the bushes right as I’m backing out of the driveway, or having to be conscious of being shirtless with the windows open.

Have an agreement in writing but give the tenant no money until their stuff is in the van or on the sidewalk, you have inspected and the locks have been changed. 

As Jon said, it's impossible to know...But, you can start with these numbers:- Assume 5 buildable lots (depending on the layout of the 5 acres, the requirements for streets/sidewalks/etc may mean that up to 50% of the land is shared space)- That puts your land cost at $80K/lot- Assume $100/square foot building costs. 

It may be wise to increase curb appeal, trimmed lawn, simple nice flowers, clean coat of pain, paved driveway/sidewalk, etc as well as a nice interior.

We will check the roof and intersection of sidewalk to building for gaps on east wall and repair accordingly.

Including adding sidewalks, curbs, alleyways, etc.