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.

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

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?  

New to real estate and have quickly zeroed in on using the BRRRR strategy in great areas, one of which I have identified as New Haven (East Rock or Westville neighborhoods).

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I would say for most people, the 1st position heloc is no a good bet, especially if you have a 1st mortgage rate of less than 5%.Using this strategy with a 2nd position heloc can be just as powerful, so you can have your cake and eat it too!