Medford (North Boston) happens to be a low supply/high demand market so I absolutely need to get more comfortable with consistent rent increases but those increases need to be researched and in line with the market. 

I serve on committees when able, and generally be understanding that a program aligned with our federal HUD is going to have it's inefficiencies.

That said, you have to be comfortable with your risk tolerance - are you going to keep yourself up at night? 

The lessons you learned the hard way in 2008 will be invaluable now, and it’s great that you’re aiming to stay small-scale and within your comfort zone of Sacramento, which gives you an advantage of knowledge in that market.Given your experience, I'd say start by focusing on three key areas to build confidence and minimize risks:Budget Control: Over-renovating was one of the big mistakes you mentioned.

That will serve you far better. 

I repeat this often in this forum; Understand how to screen, understand the community you are serving, understand the culture and treat your tenants with respect.

Would love to connect & share some resources on how to find a local mentor and id love to serve as a mentor for you in any way I can. wishing you the best!

I had two choices: stay in my comfort zone or take a leap of faith.

After high school, I pursued a career in the military, where I proudly served for seven years.

Examples might include areas in the Midwest, Southeast, or Sunbelt regions.Multifamily Properties: Consider duplexes, triplexes, or small apartment buildings to increase unit count and spread risk across multiple tenants.Short-Term Rentals: If you’re comfortable with the management requirements, STRs in vacation or business travel markets can offer significantly higher cash flow potential than traditional rentals.Value-Add Properties: Look for opportunities to buy undervalued properties where you can force appreciation through renovations or better management.Decision FrameworkRun the Numbers: Compare the projected cash flow, equity growth, and tax implications of selling versus holding with a refinance or HELOC.