I have a decent amount of start up capital for my marketing but I just want to make sure that I efficiently maximize each and every dollar so that I can build and maintain sustainability with my marketing.

Chi:Absolutely, if your debt ration supports or can sustain two mortgages then you should be ok.

The biggest challenge on this property was the budget - being as it was a property that we were living in we ended up doing things that i wouldn't have done otherwise / would have done them in a more cost efficient manner.

My insurance provider also said I can change the policy to cover STR and put it in the name of the LLC.But I'm concerned that the lender will have issue with the house being used as an STR since we secured the loan as a "second home".Did my mortgage broker lead me astray with the manner in which we secured the mortgage?

I have no facts to back this up, just a rumour that I saw on BP and elsewhere.Until there are some sustained movements showing a vacancy decrease in downtown commercial office space I wouldn't risk it, but that is just my tolerance level. 

However, FHA has sustainability rules which pretty much eliminates it as an option in the local market for anything with higher unit count than a duplex.So why invest in San Diego?

Briefly mentioned above, property involves legal, financial and civil issues that need to be handled in a timely and professional manner.

But if she is borrowing from her 401k, she probably understands it is not sustainable to keep paying 3 weeks late.

It's not terribly difficult to pierce the corporate veil, if you don't operate in a very consistent professional and totally separated from your personal finances manner.

Also, do not rely on the rapid increases resulting from COVID; these increases are not sustainable.