Can I take a regular mortgage and get a new equity line immediately after for 85% of the NEW value? 

Screening Section 8 tenants isn’t too different from regular tenants, but there are a few extra things to watch for.

So unless you need extensive work to floor plan, which changes load bearing walls, etc, then I would say, the renovation will likely be slightly more cost effective, still put you closer in rent to new construction, and provide a low maintenance property for years, given everything will be new eitherway.

. +/- 50$Current rents are 1000 per side which they say is low because it's paid off for my family member They say market rent is easily 1200 per side I would likely inherit a tenant on one side at 1000/mo , older retired single guy So if I house hacking and pay 1200 and raise their side to 1200 it's would cash flow about 150$ not including maintenance so.

Finding Deals – What’s the best way to find turnkey or low-maintenance properties in this price range?

There was a time I purchased a number of high end high rise condos; almost all maintenance is done by the condo association, further, I am able to hire the building engineer during their off hours to deal with any interior issues.  

I have several multi families on the west coast  ( one that I actually manage my self in California) and it’s just one maintenance reserve fee for all doors , and a % of the total rent usually ( 8%-10%).  

Vacancy + Maintenance/Repair figures you are using will only work for Class A properties. 

We simply include the tax on the invoice sent to guests, which makes it easier to track and ensures we're covered for tax purposes at the end of the year.For Chicago, I’d recommend checking directly with the city’s tax office or a CPA, but generally, you’ll need to register with the city, collect the hotel tax from guests, and remit it on a regular schedule (likely monthly or quarterly).

D) sets your age limit higher, I use 30 years old.just call your regular insurance company and ask them if they insure short-term rentals.