Greg is correct. 

So, if you fail to apply the correct assumptions to a property, your expectations won’t be met and it may even be a financial disaster.We use the following to rank Property Classes, in order of importance:Property Tenant Pool: closely linked to location, but not always.Property Location: closely linked to tenant pool, but not always.Property Condition & Amenities: it’s important to, “Maintain to the Neighborhood.”Key metrics for each Property Class:Class A Properties:Tenant Pool: Majority of FICO scores 680+, no convictions/evictions in last 7 years.

A CPA familiar with local STR regulations can definitely help make sure you’re set up correctly!

Though many investors bend the rules and possibly don't get caught, you have the financial situation to do it correctly.

Makes for very easy updating.As for out-of-state, @Daniel Hyman is correct that any competent tax preparer should be able to handle different state returns using easily available resources. 

I'm going to take a wild guess that those are STR or MTR rents, is that correct?

After over a decade of investing in Milwaukee I can confirm you have arrived at the correct consclusion.

You are generally correct that there is an annual exclusion for gift taxes that generally passes tax-free (of course, in all situations, exceptions apply and you have to meet all requirements to qualify). 

You are correct in your assumption that it will impact how low they can go on the down payment, though, b/c commissions will need to be paid out of closing costs. 

Does your lender only do one or the other of f/fYou are correct that paying for repairs before close presents a risk.