We as a firm have investors working with us who have rental properties all over the US big and small.Finding a real estate-focused tax professional and one who can help with advisory and grow with you would be my suggestion to focus your efforts on finding.

We both work remotely and are curious about how long we can stay at the rental before it becomes an issue, wether thats state tax implications or perhaps when our jobs should be notified that were working in WA vs OR?

If you go the medium-term route, I'd suggest you self-manage.

My biggest fear is losing a lot of money, as I'm still working a day job and living in an apartment.

Can you increase your personal income with a new job? 

She has good credit scores, job, money in the bank, etc.

However, you can suggest that they purchase "Renters Insurance", and state this in the lease that if they choose to not purchase "Renter's Insurance" then you are not responsible for any loss or damages to their property". 

The key for me has been having the right teams in place and trusting them do their jobs.

For myself, I think my ultimate goal is to have an alternate cash flow to offset my dependence on a day job, which would allow me to choose a job I enjoy rather than have to find a job based on salary and ultimately allow me to travel with family more and enjoy life rather than stress about money.Thanks in advance and hope to connect and gain wisdom!

Hello BP community I have been trying to save some money up from working 2 jobs the last couple years and I finally feel like I am in a secure enough spot to try to get into either wholesaling or flipping.