To start, something that is a "cosmetic fixer" with good bones (structure, wiring, plumbing, HVAC, roof that most buyers can't see and pay no attention to but cost a lot to replace) yet is hideous on the things buyers can see but are easier to fix and therefore add the most value ... that means ugly, smelly, dirty, dingy flooring, horrible paint colors, dated finishes, etc..

Ericka Grant It also has a lot to do with your marginal tax rate.

This HELOC means a lot to me, so it is a little disappointing to get this far and hit this seemingly brick wall.

I think I learned a lot and conceptually it makes sense what’s been discussed although as others I think $20k at a minimum level for the program is A lot to pay .

Risk tolerance and awareness of the market in stocks or real estate have a lot to do with it.  

With the information you provided, I think two of them does not apply to you ( de minimis safe harbor for 2,500 or 5000 (Hoping the expense was higher than 2500 ) and routine maintenance safe harbor- does not apply to you).The third one might apply, since we do not have info on your basis, please look into the Safe harbor for small taxpayers:You can deduct improvement on the property does not exceed the lesser of(1) 2% of the eligible building property’s unadjusted basis or(2) $10,000 Also, we should consider court cases over the years that have allowed few of the expenses related to the driveway to expense rather than capitalize. these are what court decided on few of them:Per court case, these expenditures can be deducted as repair and maintenance for the driveway, parking lots etc:1) recrowning and resurfacing with the same materials as in the road without lengthening or widening or changing basic construction2) constructing logging road on adjacent state property including repairs to tractor used in constructing the road3) patching asphalt steel mill driveway4) resurfacing a three-year-old parking lot to restore it to its original condition after construction.

He felt that was too high since he was already a home builder, and brought a lot to the table.

Sometimes I think about getting an MBA, or cert, but I listen and learn a lot to podcasts and books during my commute, and personally find that self education fills the gap.

It seems like this area would have a lot to offer with plenty of nonstop flights to RSW, access to multiple towns along the coast, nice beaches, MLB spring training, etc. 

Well I’ve been through a lot to obtain that knowledge and there’s no simple answer.