Ideally you would have a property management company coaching you through your first property for a year or so.General maintenance - high maintenance tenants generally imply higher maintenance and turnover costs.

I deal with building inspectors, subcontractors, suppliers, and laborers on a daily basis.

Ideally, this is a project I can start in July or August at the latest.

Just determine who your ideal tenant is,  be realistic, and give them what they want!  

I'm wondering about the various merits of purchasing another Single Family Home,(advantage  a multi-unit (free of any HOA associations, ideally), or a commercial property for rent to another business (not housing my own business). 

Thank you Marcia, ideally I would be plugged into a local rental association, but I guess this is a good time to start!

(Place is in great shape, and in 4 years have had essentially nothing serious happen).All that being said, I was wondering if there was a way to lower my monthly mortgage, ideally to get it down to about 1500/month so then we would be breaking even and I can stash even more cash away to buy up my next property.

2) Out of these items, which are the most important to push to get addressed:- Ceilings have minor cracks in them and seller doesn't want to address this...not ideal but should I push on this?  

Ideally we would like to continue get enough buy and holds to do this.  

I think realistically I do not want to pursue an out of area deal, and because rent is so high ideally find an off-market deal in Santa Cruz that would allow me to house-hack.