Seems like the 1031 would be perfect for you to put gains from rental sales into raw land.Land in my market is flying off the shelf often under contract within 24 hours of listing and sellers not interested in anything complicated which may hold up closing.    

. :)Alternatively, you could pay taxes on $1,000 and separately donate $700 to a charitable organization - resulting in the same $300 taxable income, however with multiple complications because it may not end up in a dollar-for-dollar offset.

I also want to make sure this doesn't complicate my bookkeeping too much.Thanks for you advice!

I'd like any recommendations on a simple app to schedule construction that I can share with the GC to keep us on track.We only have 2/3 going at once so I don't need anything complicated at this stage.Thanks!

It will complicate closings and financing, raise your insurance, and probably will not create any benefits.

However, I definitely don't have enough investable cash to cover what is owed currently and at least one source I've read says that means I would need the bank's approval of the deal.So here's my primary question: How likely and/or complicated would it be to assume the title and loan?

All these systems we have in place... there is no way one system does it all for you.. and I am not sure you really want to, even if everyone boats that is the best thing.Although I manage all these high level complicated systems, because I am paranoid, you ARE supposed to hire people and put them in charge of each system you run. 

There are a few firms that specialize in these types of investments, but they become pretty complicated in how the money works.

Thanks :) Always with partners, as commercial Real Estate Investing can be complicated and requires a team.

House hacking will complicate your tax return.Your property can be treated as both an investment property and a personal residence.