I'm in Florida which is known for having higher property taxes given that we need to supplement not having any state income taxes.

But if you just want to start a company that can supplement your income and helps you invest I would recommend other options. 

I am not sure if it's the pandemic or something else, but it seems like all Assessors are behind, I have not gotten by new property tax yet, but know that I will have a supplemental tax bill next year because my Mortgage company has based my taxes off of old data.

Given your goal for cash flow to supplement self-employment income, I'm guessing acquiring more doors? 

The contractor or homeowner then has to arm wrestle and send in legitimate bids/supplement requests to increase the payout to fair market pricing. 

We just paid our supplemental tax bill so that wiled our savings away quick.

The goal is to supplement retirement income, have fun, and leave our kids something besides an unpaid Discover bill.

The biggest piece that blew me away was that they will supplement your rent if for some reason it comes in below the rent range they provide you with for as long as you hold the property.

doing the refinance and  buying  a rental  should  be able to be processed /  approved   simultaneously ....you might be able to use one credit report and  use  credit supplements  to update  accounts as needed .....I would recommend  closing the refinance  first and then  closing the  rental property  1-2 weeks  after the refinance  closes

I know a lot of them.. they dont think about the 1% rule  they have been spoiled for the last 10 years on an appreciating Toronto market.. negative cash flow is fine with them.. their decision is based on location and can they allocated a portion of their high income to supplement their out of pocket expenses..Most of them are not so analytical on cash flow analysis like we are