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.

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

Ok yeah we are thinking of getting an investment property loan so we can stay in our current home.If we did the FHA route we are considering on living in the new property for 1 year and then moving back into our old one after the year is up.We are curious if we would get a more favorable rate if we borrowed from our home equity to buy the investment property.Do you have any idea if many investors borrow from their home equity to get started?  

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?

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.

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

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).

There are indeed many tempting short-term investment opportunities in the market that look very attractive numerically, but their potential risks can easily lead to pitfalls.

@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?