There are a few general requirements such as:Water Heaters / HVAC: Eligible systems include electric heat pumps, natural gas heat pumps, heat pump water heaters, central air conditioners, natural gas water heaters, propane water heaters, oil water heaters, natural gas furnaces, propane furnaces, oil furnaces and hot water boilers.

Notable CapEx in the 6 years are: Replacement roof, replacement boiler for Apt 2 (converted oil to gas - the boiler we replaced was from the 1940s!)

@Ethan Cooke Thanks for the response! 

In2016, the bankrupt oil refinery was taken over and is being rebuilt and is about to start production.

@David Cook, A somewhat complex twist on the 1031 might help you out - depending on valuations and how constrained you feel by those timelines and trying to purchase the second lake house. 

Hi @Dillon Cook, DM me and I will refer you to our local CPA who handles out real estate business.

How long do you think this contractor emergency call system will work if the contractor gets a call at 2am because the stove isn't working and the tenant needs an emergency pizza cooked :)Also, what if you've instructed the tenant to call this contractor for all emergencies and the contractor doesn't answer at 2am.

Even if you create an LLC after the fact and state that each party has 50% interest unless there's a filing with Cook County, your partner's interest are not really protected.

We pay for our electricity, our cable, and for the heating oil as both units share one furnace.

I change the locks right after previous tenant moves out or at the time of the eviction as instructed by the Sherriff in my area.1 - completed & signed rental application2 - all supporting documents have been submitted by the prospective tenant - copies of the following-photo id, proof of income, social security cards for anyone over 18 who will be occupying the property3 - Deposit received - at least security deposit with default noticeThe documents I have prepared upon move in- balance of funds required to get keys and sign the lease- rental package revised and completed for prospective tenant & myself to review together & sign which included lease, deposit receipt, tenant behavioral policy, move out instructions, notice to all tenants -that is a form I created which advises the tenants on grass cutting , possible liens/notices/fines from the city, what not to flush or put into the sinks (feminine products, cooking oil -used or unused), pet addendum if applicable