With either option, you will need to invest in the same or similar furniture package. 

If I were to sell and build the two smaller houses, I could likely fund them enough from my gains on the current rental (and a little out of pocket) so they also cashflow ~$300-400/mo each.So, at the end of the day It’d be a wash or a little loss, cashflow wise, on one house and I’d gain ~$300-400/mo on the other house.

Most lenders will require a minimum of 90 days, however there are some options that do not have any seasoning requirements as long as there was rehab wor completed. 

In your example if you own it outright or have a mortgage of $9.9M your taxable gain will be exactly the same.

I had a step-son who went to school at SFSU, there were occasional days of pleasant weather, but never like good ole San Diego.CA with crap weather sounds about as close to hell as we will find in this life. 

Where I'm stuck is whether I should use a metering system that pre-prints a stamp onto the envelop or find a machine that can place a physical stamp onto an envelope (obviously I can't sit there all day stamping).I'm thinking from the perspective of mail that looks to "businessy" vs. mail that looks more personalized for better response/conversion rates.

I am guessing with your trajectory that you are looking to do the same.

Estimated 45 day rehab What made you interested in investing in this type of deal?

.• 5-Bag Limit: Each resident is limited to disposing of five (5) normal-sized garbage bags per day.• Bulk Waste Limit: Residential bulk waste, construction/demolition, and green waste disposal are limited to a 5' x 8' truck bed load or small trailer per day.𝐂𝐞𝐧𝐭𝐞𝐫 𝐕𝐢𝐞𝐰 𝐑𝐨𝐚𝐝 𝐌𝐮𝐥𝐭𝐢𝐩𝐮𝐫𝐩𝐨𝐬𝐞 𝐂𝐨𝐧𝐯𝐞𝐧𝐢𝐞𝐧𝐜𝐞 𝐂𝐞𝐧𝐭𝐞𝐫 𝐭𝐨 𝐫𝐞𝐨𝐩𝐞𝐧 𝐨𝐧 𝟖/𝟐𝟔This newly renovated multipurpose convenience center will serve as the first multipurpose site to serve both Sevier County residents and short-term rental unit cleaning companies.

Recently though I have come across a major FLAW in their system, which I honestly cannot believe exists: When a payment series ends, the system archives the series on the day it ends.