For years we were renting it long term and never really had an. issue with turnover.

@Steve WrightIf it is really a rental property, then capital improvements made to it (once it is a rental) are also deductible, but slowly via depreciation and not right away.The more important issue is whether you HAVE converted it to a rental property.

Asset management is not top focus for those that are very busy at closing the next deal.For new investors: For example, a $50Mil deal can be configured to pay $1 Million (or more) day one, get poor AM, pay no distributions, forced fire sale year 3, and pay another $1 Million in disposition to GPs.

There seems to be issues with covering your expenses.Taking the sec121 exclusion, which is only for primary residences, is pretty much the best living tax exemption. 

In that scenario, Fannie/Freddie have a 15% down option (but see above about market conditions) but they still won't lend to an LLC.Now, I feel that transferring your property to your LLC after closing is a non-issue. 

A few issues I see- raising capital- as you can probably tell, this is not going to be profitable. 

I spoke with someone who had a similar issue and proved that the property was being used as a 2 unit rental because they had a lease agreement in place and never discontinued use for more than 3 years since most recent rental license.With 3 units its a bit of a tougher battle.

If the deal is good enough (i.e. has meat on the bones), investors usually have no issues obtaining financing via hard money, private money or other lending options.Your experience will likely be similar so I'd recommend spending time/effort on finding and negotiating deals.

Airbnb has insurance in place to help offset any guest issues.

Roth IRA distributions will be tax free.