A primary residence will most often provide more favorable loan terms so if you are willing to wait one year while you living in your new property and are comfortable with renting out your primary residence to a tenant, then getting something such as an FHA loan is a good strategy to minimize your upfront costs and hopefully get better loan terms.

Sounds like you need an agent and/or contractor based on your strategy. 

What’s been your go-to strategy for finding property managers that really excel?

For rentals, they can work well if the HOA is investor friendly and cash flow numbers make sense.Financing can also vary, so it’s worth checking lender requirements for condos (warrantable v non warrantable) versus SFRs

Read this post for a longer take: https://www.biggerpockets.com/forums/51/topics/1057644-augus...If you are looking for tax planning aka tax strategies, the best time to look is November-December.

You'll invoice the tenants on whatever strategy you set up in their leases.

@Peter W.From my experience, a second-home investment strategy works best when you meet lender conditions like owner occupancy and rental restrictions.

The flexibility allows investors to select the coverage that aligns with their strategy and budget.When clients receive a proposal, they are guided through their coverage options by an expert team member.

Their business model is interesting and has a couple different exits strategies when getting a property under contract.

Getting back to the original post, what would be a strategy you'd explore given his circumstances?