It's good that you have two ideas to start with.

It sounds like you are just having trouble pulling the trigger. 

@Micah Cook It's not uncommon for investors to scale up their holdings by consolidating their portfolio.

Originally posted by @Adam Apalategui:In Oregon there are service dogs or not.

Know 3 agents that were sued for NOT doing this!

Here on planet earth it takes longer than 5 hours to do that job and people who do consistent work don't work for $2 dollars an hour.

I had a similar strategy with my first few house hacks: buy in great A & B Chicago neighborhoods....get by with minimum cash flow, and wait...What's your plan for the next purchase Michael?

You may have to search a bit for the right contractor or engineer - sometimes I see one solution dominating in an area - "that is how we always do it" 

I would search the BP forums because your tax / legal related questions likely have already been asked.However, it doesn't hurt to still ask the forum what your questions are.

I think it is going to be custom to your business and its something that those who have experience with will do better at.