As you are pointing out - the expenses will all hit at some point if you own for long enough.If you buy a house that needs a new roof and a new furnace within a year... then you need to budget for those expenses in a year. 

Then once you close on the house take out a standard 30 year mortgage to pay off the hard money loan?

I found a house with an ADU (coach house) that is legal.

House was booked for the majority of June and July is looking to be the same.

However, you would have to make sure that you have been living on your current primary house for at least a year before acquiring your next primary purchase.

If I were still single, I would have definitely considered purchasing a 2-4 unit property to house hack.

You knew this going in and you still decided to buy this house.

He has also invested like this with us on a couple of high-producing STR beach houses (that net each of us around 70K per house each year).

Obtaining my Real Estate Salesperson license was driven by a desire to address the critical issue of affordable housing.

I am doing a job in Shaker Heights OH for which I currently have 150% of budget in escrow with the town housing dpt.I can only get the funds released once violations are rectified.