I save a decent amount and I already had more than enough for a down payment on a property.

Our goal is to secure properties (amount tbd) to help supplement our retirement.

Regardless of the rent, I still need to account for a low end kitchen, bathrooms, carpet / flooring, paint, as well as some amount for shared items like tuckpointing and the roof.

Also, with more equity cashed out up to a max of 80% LTV, your loan amount will rise as well.

That seems to me to be the time that you need outside expertise more than later in your career.If a deal is on the market (on MLS), the commission paid to the agents is already agreed to in the listing contract, so buyer's agent or not, the seller will pay the same amount of commission. 

It varies by sponsor track record, amount of heavy lifting and the risk.  

I did the math and here's what I found:mortgage amount = 112500monthly PI payment at 4.5% = 570.02monthly PI payment at 3.85% = 527.41difference is $42.61 per month.Dividing your points amount ($2250) by the difference yields just under 53 months.If you keep the mortgage for 53 months or more, paying points will save you money.There may also be some taxation concerns considering the deductibility of points, but I don't have that info.

A lot of state laws say you can charge the rent until you find another renter, but you are allowed to charge a marketing fee up to a certain amount to cover expenses relating to getting it rented again. 

I have a huge amount of equity in my properties. 

The requirements of the safe harbor election for small taxpayers are: Average annual gross receipts of $10 million or less; andOwns or leases building property with an unadjusted basis of less than $1 million or less; andThe total amount paid during the taxable year for repairs, maintenance, improvements, or similar activities performed on such building property doesn't exceed the lesser of- Two percent of the unadjusted basis of the eligible building property; or$10,000 (for questions about how to calculate the unadjusted basis, refer to "Figuring the Unadjusted Basis of Your Property" in Publication 946You make the election to use the safe harbor for each taxable year in which qualifying amounts are incurred.