Instead of stressing over timing it perfectly, focus on making sure the deal still works even if rates shift.Since you’re buying in Norfolk, check if lenders there offer any investor-friendly incentives.

Have recently started a renovation company with a friend, both of us successful business owners and talented in the trades.

Once you feel comfortable in running your numbers, figure out a good market that has good population & economic growth and landlord friendly laws.

Contact my friends at HomeHop Property Management. www.homehoppm.comTalk to Dan, they have a in house designer, who you can hire. 

My plan is to rent it on a short term rental basis and stay for few weeks in a year with family/friends. 

Tax accountants, investor friendly agents, 1031 exhange experts etc.

I did it privately, not telling friends/family.

It will be remote, but since you live there now, you probably already have connections who either already know the house or local friends to find you good people to service things as needed.  

Maybe a family member or close friend?

I’ve been around real estate for decades, and I read in The Economist once that in lively markets like Charlotte, folks will pay a premium for a comfortable room if you’re near major employers.A friend of mine tried something similar out in Austin a while back.. he’d inherited a 4-bedroom property and split it into individual room rentals.