We have had a Strctural Engineer out to the property and while we don't need to conduct repairs within the next 5 years or so, we will need to address both of these things at some point and it will likely cost us about 100k.Any advice on selling or holding for the long term?

Anyone have advice on general rules of thumb or ways to estimate operating cost for a short term rental new construction? 

We are not first time home buyers but have three single family homes ( rental) properties in California but want to buy our first apartment complex out of state for generating  cash flow for the long term.

We owe the lender a hefty sum due to the short sale, and my partner should be responsible for at least as much as I have paid into the deal so far.

For a house hacker, what is the term requirement for how long one has to live in one of the units before looking for the next deal?

If you sell a property in one year or less after owning it, the short-term capital gains is taxed as ordinary income, which could be as high as 37 percent.

That $400k property probably has a very short and realistic path to getting to $500k in value.

Accounting for 3% inflation, that same roof will cost about $11,423, thus if I saved only $8500, I would be about $3k short.

I'd love to try the mid term rental strategy with the property we find.

@Jay Hinrichs -- I can't wait to see The Big Short.