I've been down that path before and its not worth the time and energy. 

I'm talking about wedges of land/property that requires you to make a deal with the neighbors for access or fight for easement.I was young man, single, full of energy and life.

Different risk profile, you can argue which one is better/worse but at the end of the day you are sitting at home with a liquid asset (and lower transaction costs) instead of the headaches and energy required to renovate and manage a property. 

. ~200k Factored in. 36k-90k for car chargers. 150-250k~ energy sold to tenantsIf my assumptions are correct, I should be able flip property in 5 years or refi and do it again in 5 years @ 50/50% at 13.5m equity. rinse repeat.

Do you want to learn the ins and outs of ADU law, local energy codes, and inspection requirements? 

I spend a good deal of time working on my finances but that takes a LOT of time and energy!

***NOT taking off the old shingles, is only saving you around $1K (give or take)... if you're already going through all the hassle of new system, bite the bullet and do it correctly.When you remove the old layers, you can then: do any necessary repairs; possibly install ISO boards (insulation boards) smoothly; install the good membrane (not simple felt!)

My W2 career pays well but leaves me exhausted with little energy for my family which doesn't feel good.

you should get a RMLO or an underwriter to qualify the borrower. if its owner occupied and in florida you also will need to use a third party servicing company to service the loan which will run you around $450/yr. not an accountant but its my understnding unfortunately the interest income is going to be taxed at ordinary income and the principal will reduce the principal. how you offset the losses talk to your CPA.your best bet honestly is to just sell it and bite the bullet. 

Hello BP community, I'm starting in the Real Estate world as a flipper, I'm putting all of my efforts an energy building an experienced team therefore I need help with Leads.