Since most downtown buildings do not allow for STRs (per their HOA), you are really only left with long-term rental or the occasional mid-term rental if you are set on having a downtown loft.

This includes maintenance/cap ex, vacancy, PM (even if self managed), PITI, HOA/melo roos, LL utilities, and miscellaneous expenses.  

Add in steep hoa and possible hoa restrictions. for those who have made investments in either location, what do I need to consider besides profitability that may be a deal breaker?

HOA typically covers that because it’s a common expense. 

Duplexes hv a bit more optionality i.e. 2 units vs. 1, you don't throw money at an HOA every month that isn't tax deductible, and you can rent out 1 or rent out both.

But after crunching some numbers and noticing high HOA+fees, in today’s tourist economy after COVID, I’m not sure if it would profit enough to surpass the current LTR, especially when the LTR in San Diego market also has the potential for future value appreciation.

This means you likely won’t meet new neighbors at your next HOA meeting or invite them over for a barbecue, but there are still many ways that you can make newcomers feel welcome!

So far here’s what my assumptions have been:annual taxes (published in MLS, around)insurance (around $1740 annual, which may be a bit too high)HOA/condo fees.

These will generally have a few options at about the $300K mark, every now and again their is a neighborhood in Lake Ridge (22192) that will have a a sub-$300K option (expensive HOA though). 

Hello BP,I am curious... those of you who are using Buildium for HOAs, what do you use for your property management company's bookkeeping?