Good luck on your adventures

I haven't purchased this way before, and unless you can gamble a bit of cash without having a contract, I wouldn't suggest it.

They may want to gamble on someone else not knowing the 20 year old HVAC, but as you mentioned, it's going to come up during the inspection.  

Fortunately, the calculated gamble had paid off.

I would assume so, e.g. you have a $100k home loan, take a $30k refinance out for downpayment on another adventure, now you own $130k. - I also see people tend to use some sort of formula to determine if a rental will be cash flow position, where they factor in repairs, capex, management (i think to do that part myself), etc.

The Multifamily properties need more than cosmetic work as they were foreclosed for years and winters are unforgiving (unheated building, etc).It has been an adventure.

I don't see huge upsides as there is only a few years left in the up swing and after transaction costs, it's not that fruitful to buy now and hold for another 5 years or so.Also, I'm in earthquake country and insurance is a gamble at best as they may deny a claim.

Hello Sara, I'd be happy to help with your adventures here in Milwaukee.

Being a middleman- Realtor, contractor, ect -and get paid off the "investors" gambling. 

It's an an adventure but it's an amazing adventure.