I turned the extra room without a bathroom into a workout room as a bonus amenity.

Hey William, what about adding another partner that has experience doing larger deals? 

As the 3rd largest MSA in the country it's hard to generalize the Chicago market as it's actually over 100 different submarkets when counting the 78 communities in Chicago property and then adding in the various suburbs, including in and around Naperville. 

This added demand for rentals drives up rents.You must invest in a city with significant and sustained population growth to have rents outpace inflation.

Then use the extra roommate rent income to pay down your mortgage and look to refi to a lower payment in the future (3-5 years) - so it cashflow when you move out.You could also choose the smaller unit and STR the other unit to generate more cash to pay down your mortgage and refi, so it cashflows when you move out.Bottom line: you'll have to get creative to solve your cashflow challenge!

See my long list posted earlier of the issues adding an ADU.Good luck

A capital improvement is not - it gets added to the basis which ultimately reduces the tax due on sale but it’s not tax deductible in the sense in reduces current income. 

Hello there community, in the recent days I have been teasing the idea of house hacking if I decide to move in the future  in SLC ( love skiing and the nature).  I have read the city’s guide https://www.slcdocs.com/Pl...

Without complete financials up to that point, extra work (and headache) will be required to get everything straight after years of failure to keep complete financials.There also might be an asset protection wrinkle by not maintaining complete books for an LLC, but I won't comment on that as I'm not an attorney.

PPC and paid-ads for larger companies