Why is the Seller selling the property before fixing the roof?

Did you sell, did you just continue to rent and accept fines/penalties, did you shift to mid term or long term rental?

Even if nightly rates didn't continue to rise over time, breaking even now would still be a free house in 30 years that I could sell and use for a retirement nest egg along with my 401k.

FOLLOW THE K.I.S.S method plan (keep it simple and stupid).Find and hire a real estate agent that understands multiple investment strategiesGet pre-approved - see what options you havebased on your pre approved price - identify an area you want to invest in that you can affordLeverage the agent to : bring you properties, assist in pulling comparables (you should know your comparables of the area you are looking in, this is for a second opinion) review and confirm your estimated rental income, assist you with acquiring the property, and have a list of resources you could use; contractors etc.Looks at properties and make offers that work for YOU.Also,Do not pull your IRA money out, leave it there and let it grow - leverage this to meet your lenders reserve requirements.Buy Multi family to holdBuy single family to fix and flip and produce more income to buy more multi families.

These podcasts have something to sell you and you're biting the bait.These forums will educate you quite aggressively, and if you sit down and go through them you'll get expansive knowledge for free.

We have about 66,000 duplxes, but not many are for sale (because why would a small investor ever sell a duplex?)

The highest rate we offer is 13%, I don't know how you'd do a 15% rate, those coupons aren't selling in the secondary market.It's not a one size fits all whether a HELOC or Cash Out is better.

They would need cash to buy/rent seasonally in Florida, so is there a scenario where they sell the house to me, obtaining the cash they need to buy in Florida, and then rent one of the units back from me in the summers?

I'm working on calling a list of event planners to see if they will share any information.As long as I have a plan before renovations, then I think my worse case scenario is that I spend some time, learn some things, and sell it.

A lot of owners already panic selling at discounted prices / price cuts.