Hey all, for those of you who have/had vacation rentals that started off great but the location is now not as desirable for tourism, etc.

i know there's great opportunity if the island expands its tourism marketing and atracts more visitors.

Despite increasing tourism for several years running, income was stagnant or dropping.

Agreed with Paul...embrace the *AND* not the *OR*... :-)Also, it's not just about the money...Personally, my personality suits flips more than wholesales (I don't like marketing, and can farm this part out for retail sales but not on wholesales), so I'd rather do flips even if I made the same amount by wholesaling.Wholesaling is something I could do if I had a partner who could compliment my weaknesses...but barring that, it doesn't matter how much money I could make, I'd be miserable doing it on my own...That said, I think someone who builds a wholesale business in a well-structured and scalable way could do quite well with it...probably just as well as flipping given the same amount of start-up capital...it's just a different set of skills...

When working with clients' tax advisors, oftentimes we have to educate them on the subject.There are tax rules that apply to such plans about which you must be aware, but it's a great strategy for those that embrace it.Key items that you should be considering as you invest are prohibited transactions and UBIT.

Now unless lending in Michigan is at the point where bankers are full on embracing the 2008, I can't see any main line bank willing to work with you and offer you the the numbers and ratios you proposed in your initial scenario.

Talk to the Better Business Bureau for the area to determine what level of tourism is for the City.

Another method that no one has mentioned, is buying homes in an area that has high tourism and then AirBnB some property. 

Technology is really good at aggregating data, but aggregate data is not in any way relevant to this particular house right here you are thinking of buying.What technology, exactly, are you suggesting be embraced? 

Relating his income to something that is beyond his contro (% of collected rent) will probably be a difficult concept for him to embrace.