Hence, your goal should be staying on the first page as long as possible instead of picking up a few bookings from different places.  

Otherwise with the dwindling tech sector in SF, and the remote work (2-3 days a week) that is most likely here to stay, it just doesn't seem like a strong mid term market to me.

I’m curious - are you leaning toward staying local in Connecticut, or are you open to exploring oppurtunities in out-of-state markets like Phoenix?

Make sure to stay on top of things and don't trust too many people (especially the so-called experts). 

If we stay with our high-paying jobs, we can carry the properties, but we(spouse and I) are too afraid to invest in Class B or C neighborhoods.

You need to know how to analyze property and then systematically evaluate property on a daily or weekly basis to stay on top of the market. 

I stay away from curtains as they can get dirty easily but I update the shades themselves to something nicer (plantation or shutter like shades or good quality roll down shades - black out in the bedroom).

I stay away from LG and Samgsung.

@Rae Chris Ann Arbor is pretty expensive, so difficult to find cashflowing rentals.You may want to look in Ypsilanti - if you want to stay in your area.Otherwise, Metro Detroit offers a LOT of options.Read our copy & paste below for some helpful info:---------------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

After five years, I am willing to buy the other owner out or they could stay in and continue earning and enjoying the property.