It means that you, as the purchaser, cannot close on the purchase of the property until (subject to the terms of the contract) the seller identifies a new asset to acquire with the proceeds of the sale. 

Without rent control i either raise their rent far above market rents so they give me notice (my preferred method) or i simply do not renew their lease.

There is a "sponsor exemption" but that only allows an unlicensed person to raise money but it cannot be more than 50% of their duties and the pay they receive cannot be based on how much they raised.If you have never raised $, a family office will be off the table as they typically want the company to ahve atleast $50-$100M in assets. 

So if I am looking at an asset as a 10 year play - I look more at the location, schools and how has this market performed in the past excluding covid and 2008 which were extenuating circumstances.Reality is right now shorter term plays do not work based on numbers and cost of financing - we went through this same thing in 2001-2004ish timeframe where properties would appreciate 2-3% per year and after buying costs and closing costs - you were not making money on assets unless you performed the labor or found a really good deal.this is how real estate "typically" is - which is why everyone always says location location location - because after a decent holding period, you will win.

If you have a mortgage the lender will require you to have insurance that protects the asset that secures the loan3.

I agree with complications of ownership when it comes to Land Trust, and it also does nothing for asset protection. 

If you analyze everything right, observe your mentor and take your time to get the right asset, it will be fine.

I do have folks that don't book because of that.That is a good thing as not understanding the distance to get places will create bad blood and cause those 2 and 3 star reviews which no one wants to see.Like @John Underwood, our place isn't cheap so we don't get the folks that destroy places.The bottom line is that you are renting out an expensive asset to strangers for 3-10 days or whatever.

I suggest having smart TVs and let them log into their own accounts, preferably with a guest mode so they auto-log out after a certain number of days.For catering to families, I would concentrate on providing amenities like puzzles and games. 

Read some books, preferably those written prior to 2015 when YouTube gurus started telling everyone how easy it is to buy 17 houses a year with no money down.Investing is pretty simple if you just follow the process investors were using since the beginning of time.