Current lease term (expiration date, month-to-month)7.

The better location house is something that could be used as a short term rental too and or we have considered just keeping it for ourselves at a later date.  

Team,Im having a tough time finding an insurance provider for my medium term rental in Pittsburgh and I'm looking for suggestions.I own the building (triplex) where 2/3 units are traditional long term rentals, and 1x unit is a medium term rental.

I would encourage you to also have an attorney prepare Application Terms & Conditions. 

You picked the wrong kind of property to start in as a 3/3.1 townhouse is not ideal for room hacking and is more residential in nature which is why you should sell it and take the proceeds and deposit money and look for a two-family where you and your brother can live in one side and you can full rent the other side - maybe even as a mid-term rental to 2x the rent.

The long term goal is to rent out to tenants long term and scale into multiple properties.

Appears to be a well oiled machine in terms of the construction and sale process-cookie cutter 1200 sq ft properties.

Most work this way Rates: 9% to 13% (Most Deals are 11-12%)Terms: up to 36 Months (Most Deals are 6-12 months)Fees: 2-4 points(%) of loan amount paid at closing (Most Deals are 3 points(%))Minimum Loan Amount: $50,000 (For loans less than $250,000 $2,500 minimum fee)Max Loan: 65%-70% of After Repair Value(ARV)100% Rehab Financing Available (Require 20% of purchase price down payment or cross-collateral)Closing Timeframe: 48 Hours - 3 Weeks (Most Deals are 2 Weeks)NO PRIMARY RESIDENCES, NON-OWNER OCCUPIED ONLY, BUSINESS AND COMMERCIAL USE ONLY.

I currently have 5 mortgages but have not been great at keeping track of the details such as costs associated with each individual property.

Factor in costs such as:Property taxesInsuranceMaintenance and repairsProperty management feesVacancy periodsLong-Term Strategy:With plans to acquire multiple properties, develop a clear long-term strategy.