Do you want to put all the money, time, and energy into owning this home/investment?

You just lose out on the efficiency created by the 1031 structure.   

Sounds like it's possible to buy investment first, but probably more efficient to work on owning my primary.

i bought a home warranty once and never would again. they rarely have things taken care of in a timely manner, which can be fine for your primary in some cases, but not for a rental. and the companies they contract to do the work, are getting paid pennies on the dollar for those jobs based on the deal they negotiated, so they're in NO rush to get out to you. and like any insurance company, they do all they can to get out of stuff. it was a waste of not only money, but also time and energy.

Animal control broke the door and the apartment was destroyed, the energy was shut off so the fridge was full of magots.

Here are some of the options we are considering:1) Keep the system basically as is, but update it for greater energy efficiency. - Install two new high efficiency condensing boilers, and update windows and insulation for better heat loss performance.PROS - a) minimally invasive; b) can provide 15-30% reduction in heating costs (we are told).CONS - a)total gas expense is still paid by the landlord; b) individual units won't have individual control (except for a thermostat controlled shutoff valve for heat/water in each unit); c) AC would be available on with in wall/window units. 2) Try to individually meter each units' gas and provide each with a traditional forced air heating/cooling system.PROS: a)gas expense could be completely removed for landlord (huge)- even tankless hot water could be installed in each unit; b) each unit would have their own climate control.CONS: a) constructions costs of running new gas lines and soffiting sheet metal duct work. b) highly invasive with collateral construction costs; c) future costs of maintenance on multiple systems vs a single building-wide system. 3) An electric based heating system- This is tricky in my mind because of the high cost of electric heat.

I am using their in house CRM as it is very efficient and easy to populate deals. 

The time and energy you will spend pursuing a remedy is not worth it.  

Shelter and energy were the standouts, contributing over 60% of the monthly increase.

It's just about efficiencies.1month per annual lease is normal @Amirra Besh you're investing in the greatest city in america.