Property was well maintained &reasonably updated with refinished wood floors, updated bathroom, newer appliances, dual pane windows, and modernized heating/cooling systems.

So when I spoke to one lady about a mortgage after looking at tax returns it seems my DTI is not favorable for the mortgage. 

@Mike Bianchi I would look at the Yale optimum asset allocation portfolio.You have enough wealth to not be all in with real estate and a little diversification at this stage will reduce your risk, according to Modern Portfolio Theory.I would recommend this allocation, it’s also available on the Financial Samurai website:1) 35% Low Cost Stock Index Funds2) 10% Low Cost Bond Index Funds3) 25% Real Estate4) 10% Cash5) 20% Alternative Assets (Private Equity, Passive Real Estate Syndication, Hedge Funds, Precious Metals, etc.)You may also want to do some search terms on Google like “All Weather Portfolio”, to understand how to allocate your wealth in a way that will have you sleep at night while making you richer.

What I'm gonna do is allow the 85 year old lady to continue using the driveway across my yard, under the form of  a revocable license, up until such time that she no longer occupies the residence / or the deed transfers to a third party (probably a trust to her kids in this instance, or maybe an unrelated 3rd party buyer), at which point the liscense will be revoked and I will remove the improvements (asphalt) and restore the benefit of green space to my property.Perhaps more likely---- the neighbor ---- or the eventual 3rd party buyer---- will want the benefit of that driveway so that they can access their house (other than the public street out front with no parking) and I'd imagine they'd either A) buy my property from me or B) pay for a lifetime easement to be able to continue to use the drive for access to their house.      

Purchase price: $80,000 Cash invested: $60,000 4 bd 2 ba 1,866 sqftThis newly remodeled home boasts a modern feel as soon as you walk through the door!

Handing some 92 year old lady a disclaimer and stacks of agreements may not do anything for you!

And until modern history you are right - we had servs and we had the ruling class.

If you need to update to modern code it may have to be all surface work( conduit etc.)

If you start looking for a vehicle before you actually need it (i.e. while your existing vehicle is still serviceable), you can find wonderful deals - my current work vehicle is a Jetta TDi wagon which was 18-months old with only 16K kms (10K miles) {just past the first oil change} when I bought if from a lady who decided she "needed" an SUV.  

You can definitely spruce the place up by buying ikea furniture and making your Airbnb more modern.