She wields a lot of power with your tenants and right now is turning them against you.You kind of "ripped off the bandaid" with your strategy, which will cost you some money in the short term, but may still work out in the end if you can absorb the negative cash flow.

I only know the big companies and they're quoting a lot higher than I usually pay here for similar roof. 

I have had multiple investments that I started with negative initial cashflow and have done very well as rents and value have appreciated. 

I’m going through a REFI now and the bank is asking for everything except my recent COVID test (negative).If you are still reading, thanks for not getting distracted and pressing through!

I would like advice on our only property that currently negative cash flows 450 dollars per month.

I'm in a Hot Market with high prices where Cash Flowing properties are rare (Montreal, Canada)Would you be willing to take a deal with negative cash flow for the first 5 years (2-5K $ per year) if it offers:Appreciation potentialEquity accumulation ( Around 250K over 5 year)And tax benefits + deduction (Around 60K / year between operating expenses, loan interest and depreciation) ? 

I only got that the feeling that they were slow , busy , and easily annoyed. 

I only have 3 rentals at the moment. 

So you need 2 years taxes for a lot of lenders to negate a rental property.

The issue is I only ever spend 1 week/month at most in Milwaukee, so I’d essentially need to buy these properties sight-unseen.