This bodes very well for the mountain resorts.- Vacation home sales have doubled in the past two years..

I understand some of their frustration but resorting to calling me too overweight to look at problems have pushed me to the breaking point I have not allowed them to see.

Resort to sanding the walls?

Same way I'm not gonna attend the time share pitch even if the Jet Ski rental is free after it. 

For instance, take a homeowner who uses a vacation rental manager to rent her home in Destin, Florida, a beach vacation hotspot, but then buys a house in Aspen, Colorado, a ski resort area.

So, I doubt we will have the same income in the future from that condo.A few years ago, I wanted to get an ocean front unit at a really nice resort in Myrtle Beach but was not sure if it would make financial sense, so now we are back looking at both Myrtle Beach and Fort Myers Beach apartment/hotels.

Some places in Canada, such as NB and NS, have security deposits; others, such as Ontario, allow the collection of last month's rent, but no security deposit.Regardless, when the tenant is still resident in the property, you do not resort to the security deposit, you repair the damage and invoice the tenant immediately (with the invoice due at the time of the next rent payment).In this instance it seems as though you may not be able to prove the tenant is responsible for the damage.  

I'll try to resolve it first and refile as last resort. 

As Brian and Doreen already mention, just putting it in a different way... make the decision only after you see the impact based on two aspects (1) the larger picture of your portfolio, income and taxes and (2) the impact to the IRA in terms of cashflow needs for the property.With regards to the DOL PTE 80-26 exemption, please use this as an extreme last resort as there are many a documentation that needs to maintained as justification for the DOL and the IRS (more than the requirements of any custodian).

On my $300K example above it will most likely cost you about 10K to 12K.If your deal is good enough and the extra $12K is still getting you a well priced property that will cash flow then this route might be better than no deal at all.But I would hussle with as many brokers and bankers first to try and get a decent long term loan before going to HML which should be a last resort.