Let’s start with the How.

My personal insurance nightmare started on Sept. 10th and required $120K in improvements during the past four weeks.

Or do I want to take a general concept and start working on getting the funding under way?

It's starting on 8/17 but if you buy before most likely seller is paying the commission.

The reason why I am asking for advice on this, is because I just now started to save for a down payment on a house and I am looking to move into my first home next year. 

If you just hire the cheapest or first PMC you speak with and it turns into a bad experience, please don’t assume ALL PMC’s are bad and start trashing PMC’s in general.

(We were planning to move back to our rental and rent our primary due to higher rents so started to rehab the primary then found out insurance would not insure us due to the high fire risks if we changed so ended up rehabbing both houses and burned the savings).Our dilema is we don’t want to sell either of our current houses due to excellent locations and appreciation potential but want to progress with more rentals.

Mind you real estate attorneys generally start around $300+ per hour. 

As a hard money lender who works with many investors in the Portland area, I can share some insights on maintenance costs for multifamily properties in this market, though individual experiences may vary:Lots of investors report a slight decrease in maintenance costs during winter months, bc of:- Fewer landscaping needs - Less wear and tear on HVAC systems (as heating is generally less intensive than summer cooling)- Reduced tenant turnover in winterWinter-specific issues can arise:- Potential roof repairs due to heavy rain or occasional snow- Gutter cleaning and maintenance to prevent water damage- Heating system repairs or maintenancePortland-specific factors:- The mild climate helps reduce extreme weather-related maintenance issues. - Older housing stock in some areas may require more upkeep. - Strict local regulations can also sometimes increase compliance-related maintenance costsCost-saving strategies I've seen help:- Preventative maintenance programs can help reduce overall costs obviously - Some investors report success with in-house maintenance teams for larger portfolios- Energy-efficient upgrades can help reduce utility costs in the long runYour specific costs will depend on factors like the age and condition of your properties, your management style, and the specific neighborhoods you're invested in, but hope this helps!

I think starting with a mutil family, adding value to it (making improvements if needed and raising rents), is a great way to get started.