However, for the taxable account, what would be my options to limit my tax basis (as well, how would I be able to calculate what my capital gains would be - is there a simple way to do so?)?

The properties have appreciated more than that over the last few years due to inventory shortage and limited appreciation the previous several.

This may or may not make sense depending on your ratio of days on the road vs the property.If you do go with SC, I would again recommend looking outside of city limits (doesn't have to be in the mountains, just not the city itself).

Things get ugly from there.In my early days, I used to accept multiple unrelated tenants as long as it didn't violate my occupancy limits of two adults per bedroom.

I realize I am giving limited info...and can give more if needed.

Is there anything you can think of that we might run into with this that would limit it as an investment?

If you are new to the concept, a series LLC allows you to form one entity, pay one filing fee but create an unlimited number of sub-entities that are fully separate for liability purposes.

You might need to show them how that works on paper and that financing will likely make more money and spread out their income tax liability instead of claiming it all the next year. what you do not know until you ask questions to all possible lenders, especially all of the fees they charge. 

Whats the price limit your looking at?

-My second RE agent just wanted me to buy, she knew what my spending limit was and she would always try and get me to purchase at my max budget.