or should I bite the bullet and invest it all in this ridiculously expensive market because we love the area and at some point you just have to get started?

When you are feeding your mind there is so much information to work you way through and it takes a lot of energy just to sort it out and get a handle on the big picture. 

Upper main roof first half replaced 8 years ago, second half replaced last year, and lower roof was replaced last month.4 Separate Crown Aruba Gas Boilers, regularly serviced and approximately 20 years old. 4 Separate Gas hot water heater (ages vary)Washer Dryer hookups available in basement for coin laundry for additional incomeExterior painted two years agoShingle sidingProperty just passed state inspectionReplacement energy efficient windowsPurchase Price: $210kAppraised Value: $285kProperty Type: Quadplex/Turnkey tenants in placeArea: BUnits: 1-3BR, 3-1BRRental Income: $3365 Per Month / $40,380 per year (rents can be raised 5% upon lease renewals)Utilities: Separately metered, each tenant pays their own gas and electricHouse Utilities: Common area utilities are about $20.00 per monthWater/Sewer: Landlord pays $1500 per yearProperty Taxes: $7855 per yearInsurance: $2500 per yearLandscaping/Snow removal: $1221.00Vacancy: ???

Deed in Lieu = Zero EquityWaste of time and energy.

I ended up spending tons of energy over the course of a year fixing tenant-caused problems that were absolutely out of line with our lease contract.

Or should I bite the bullet and look to purchase the SFH?

Just need to brainstorm with anyone interested: We've put a great deal of time and energy into marketing our properties for sale.

Convey to the visitor exactly what you do in bullet point format.

Are you actually lowering your own dollar per hour earning potential chasing these unicorn deals when you could spend that same time and energy on something more realistic?

At the beginning of a low budget campaign or any brand new campaign for that matter is to focus all your energy on making sure your search terms are properly optimized.