But I'm getting substantial pushback from family exactly for being on-call like that for so long.

As far as the bedbug cost, I would consider how long you are willing to let the place sit empty. 

As far as building homes goes that is something I would like to get into down the line l, I’ve been doing construction as long as I’ve been working I would just think I would have to build a solid portfolio before even getting into that.

I have some upcoming repairs needed that outweigh the Homestead Exemption and plan to make my primary home a long term rental in the next 7 years but the repairs can’t wait.  

In particular know exactly what you negative equity position will be and how long it will take at conservative cash flow numbers (near 50% of rent going to expenses other than P&I).  

This is how long-term success is built.

We have 17 properties and the long term we do on ACH, but frankly, ACH set up at our bank is so cumbersome that I stopped using it for the mid-term market.  

The city’s robust economic growth and steady population influx continue to drive strong rental demand, making it an ideal choice for long-term investment success.Best of luck!

However, I probably would not upgrade it but I would rent it out LONG TERM at least until you know your long term status in Portland.  

Let's look at each:MATERIALSMaterials are actually the easier of the two to understand & monitor - as long as there's a decent amount of transparency about the materials needed. - Once an owner knows what materials are being used, they can then check pricing at Home Depot, Lowe's, etc. - Some materials for bigger jobs, like concrete, are harder to check pricing on.