Also, what is the age of each building and the major systems?

The lender I spoke with in the new area said our DTI is the biggest issue, and that selling one of the properties would solve that problem, but selling one house hack for another of a similar price/cash flow isn't something I want to do.Still fairly new to REI so any and all advise is greatly appreciated.

You can definitely get cheaper ones, but we've had durability issues with really cheap ones, and even a lot of them arriving with cracks in the surround.

I super managed the property – income, expenses & loan - and took care of all maint. and mgt. issues (the water damage was handled through the previous owner’s property ins. ) and brought the occupancy to about 100% while raising rents about 20%.

Failing to claim expenses can lead to mortgage fraud or even major tax issues if you get certain refundable credits.Not worth my time to comment further.

Thank you for the literature and will cite AB 68 (as it is for Water connection) when addressing this issue with Oakland Building Department next time i speak with them.

Usually, the issue here is the land.

Licensable vacation rentals are obviously in high demand and offers can become quite competitive, I don't have any formal statistics but I'd say a quality active or eligible vacation rental sells at least twice as fast as a non STR property, the majority within days..My best advice to investors shopping for a hot or high demand asset class is:- Prepare & Practice: Get your ducks (GO UO!) 

I am worried that purchasing the property and then transferring it to the LLC will trigger a due on sale clause that could cause issues after purchasing the property. 

That being said, the bigger issue I'm seeing right now is Beyond conservative and leaning toward fear based investing.