Also, with the recent settlement (Airbnb and HomeAway) PBC Tax Collector strictly enforces STR tax registration policy.  

Consider using an attorney for the note and settlement.

If the amount of repairs is less than 15% of purchase price of the house (in this case roughly 61K) you could choose to identify vendors and have specific contracts with them for the repairs and your intermediary can instruct the title company at closing to put those items on the settlement statement as sales concessions and checks cut directly to the vendors.  

It wasn't very well done, but it was done.You could have sent the landlord a written notice that you wanted to see the settlement for your deposit.

I'm looking over my settlement statement from house 1 to understand this more.  

HUD-1 Settlement Statements of the deals they've supposedly done.

Here are some of the options for investing your retirement accounts: * Real Estate - including apartments, single family homes, and duplexes * Commercial property, developed or undeveloped land * Mortgages/Deeds of Trust * Publicly traded stocks, bonds, mutual funds * Private Limited Partnerships * Private Stock Offerings, Private Placements * Private Limited Liability Companies * Secured and Unsecured Notes * Judgments/Structured Settlements * Tax Sale Certificates * Car Paper * Factoring * Accounts Receivable * Commercial Paper * Equipment LeasingYou can also set up Self Directed Coverdell Education Savings Accounts for child education expenses and Self Directed Health Savings Accounts for health care expenses.What if you had a child who was 5 years old and you opened a Coverdell account for them with $500.

@Amon PlylerYou could add him to the deed of the properties after settlement (or possibly before if the bank doesn't need his qualifications), and decide on what percentage of ownership each of you have that you feel fit.And if you feel like you need more than that, you can form an LLC together with an operating agreement - which you can get really specific with if you choose (roles, responsibilities, compensation, buy/sale agreement etc).

When you consider that you got $3600 ($100 per month using your numbers) in cash flow from the property and then put another $23188 in your pocket at settlement, is the tax bill really that bad?

as a means to expedite the transaction, ask the wholesaler for a copy of the Settlement Agreement from the title company - - it is prepared the day of COE.