also for cars, don't trade them in frequently. 

They keep having you send money but I found out the money was going to someone they had to turn around and send to Bitcoin.

But not sure trading 1 job for another is what you are looking for (although 1 may allow more freedom to not have to be in the Library every day). 

Sometimes in the bigger cities that have a decent amount of land trades/sales, if you talk to brokers, you'll get a sense of where they commonly trade at, i.e. 50k/door, 100k/door. 

Its much faster to communicate/discuss with others, e.g. my realtor and supporting trades.  

Im willing to live in 1100 sq ft for a year my wife and kids are not so thats the trade off i thought i had to make in order to use owner occ financing.

There are trade-offs to all investments, I moved out of CA to Nevada because of the tax benefits and it's a much more landlord-friendly state.

So I totally understand how to add value to a rundown property by doing the work myself -- it's good old-fashioned sweat equity (more properly termed "trading time for money.")What I don't understand is how it works to add value (at least profitably) by hiring it out.

Solar, restoration, construction, or any kind of trade company.

Point being, perhaps the roof work could be considered just a repair, and you write it off, and ignore my options 1 and 3.3) For a commercial property that is a "trade or business", you can take a 179 deduction on the new roof.