Quality small multis that do come up in market have multiple offers w a FHA loan you will be in a disadvantage vs applicants w all cash or w conventional loans offers.

If you are confident you won't get lured into something out of your cash price range, that would actually become a disadvantageous strategy if I'm objectively providing advice on account of unnecessary interest payments

Is there any advantages or disadvantages in starting with a smaller home?

Taking a good look at your average income and average expenses gives you a baseline to build on.Starting out as an agent has its advantages and disadvantages.

I am only providing an opinion here, you are still best to check with your accountant to understand the advantages and disadvantages. 

If anyone could give me some advice on the advantages and disadvantages of having a rental property with a pool, I would greatly appreciate it!

I understand it's possible that interest rates would be higher than putting down 20%, but would there be any disadvantages of putting only 10% down on a vacation rental other than interest rate?

I'm not getting the house at a steep discount like you do so that's my disadvantage but my advantage is the property is currently occupied.

No doubt the bank has a much better idea of the property's worth than you do at this point, which will put you at a disadvantage.

I could claim the $100 as expenses.Is there a disadvantage in doing this?