If needed you could just delay building till closer to retirement. 

We closed yesterday- the house is 90 miles from where we live (Aspen-so buying closer is not an option yet.)

FYI in cleveland when the city sees the owner as an out of state entity you are put right in the cross hairs and they will literally go measure the grass and fine you and make it a criminal offense. so in cuyahoga county yes i agree to use a LLC but I would do an ohio one.

IM CLOSER TO NH COUNTY, FROM A STRATEGIC STANDPOINT ALL ROADS FOR ME LEAD TO NEW CONSTRUCTION 2-4 UNITS.

Should I just raise it a little per year to get it closer?

I have heard Texas and most areas would be closer to $100 when its all said and done.You can find good contractors through realtors, HBA in your area, REI Facebook groups and meetups etc.Make sure to check references of past and current clients, visit some jobs in process as you can tell a lot about a contractor by how the job site is kept up and organized.

But our winters are more brown grass season now.

All those areas you mentioned sound South, what about North closer to Northeast Philadelphia Airport?

You can't go by a checklist and say " Tall grass?

Ok so the next update on the 1522 Latham 38106 project.After a series of storms rolled through the area, the grass was not cut in a timely fashion.