Buying two businesses back to back (small local one first, larger remotely managed one second)

I'm a self-funded searcher based in Los Angeles and I've found myself in an interesting position. Actively pursuing two deals at once with very different profiles. The first is small and local. Sub-$350k, compliance-driven field services, Southern California. I can manage it while still employed and use to bridge my income once I separate. It's not the dream deal but it checks the boxes and the math works. The second is the one I'm genuinely excited about. Industrial services business in New England, 50+ years of operating history, virtually no competition in its niche, owner is almost 80 and ready to hand it off to the right person. No broker involvement so I'm in contact with the owner directly and we've already had a couple conversations that went really well. The kind where you hang up feeling like you're talking to the right person. The plan is to close the small one first, get some operating history under my belt, and close the larger one 4-6 months later (or more, I'm not in a rush) once diligence is done and the financing is fully in place. Two things I'm curious about: 1) Has anyone done a two-deal sequence like this? How hard is it to manage two businesses in those first few months when you're still figuring everything out? 2) When you're working with an older founder who doesn't use email or engage digitally, how do you manage diligence? I'm thinking the accountant becomes the main point of contact for financials. Has that worked for others? Open to any perspective (especially the cautionary ones).