And I understand that larger scale operations increase their capacity by having teammates handle specialized roles (maintenance, bookkeeping, etc).But I'm curious... if I start my own Property Management business... how many units can I manage before I go crazy?

I recently had a bookkeeper from India, setup QBO for my 4 rentals.

The ideal extent of involvement would be a few hours of bookkeeping each month and fielding the occasional question from a property manager on how something should be handled.Clearly, 1 or 2 homes would be too few and not allow you to smooth out cash flow over time. 

I eventually moved to Quickbooks as the bookkeeping became more nuanced and I wanted to track basis properly as I executed 1031s.

I don't see anyone including overhead - either their own time or other 'running the business' costs they have and allocating them to their rentals, nor do I see others allocating administration - for example costs of attorneys, CPAs, bookkeepers and upkeep of LLC holding companies to their rentals.Am I missing something or are we just ignoring these expenses and not figuring them into our calculations.  

I am a bit skeptical about that number, so I am running my analysis based on $500/mo and if we can get $600, it'll be a bonus.Estimated Purchase Price: $115,000Down payment 25%: $28,750Estimated closing costs: $5,000Estimated mortgage: 4.5% for 30 years = $437/moEstimated renovations: $15,000Monthly Revenue: $2,200Management (10%): $220/moProperty Taxes: $165/moInsurance: $160/moMaintenance (10%): $220/moLawn care: $150/moVacancy rate 10%: $220/mo (estimated high)Income - Expenses = $628/moSo that is $7,536 cash flow annually with an estimated $48,750 cash outlay means 15.4% cash ROIHere are some pictures of the building as it is right now:I know these aren't the best pictures, but I will post some better ones once the power is back on and we can get some good shots.I am also looking for an attorney who can help with LLC formation and advice as well as an accountant for help with bookkeeping and tax prep (not just for our rentals, but for a salon & spa my wife owns), so if anyone have recommendations, please let me know.  

I suck as a book keeper (and I hate it).

With the income I should receive with 30 units, should be enough for a property manager, bookkeeper and nice profit for me and business partner.At the end, only time will tell.Any other question?

Keeps things separate for bookkeeping and records purposes, as well as providing the extra layer of protection, like @Nathan Click mentioned.

Keeping each property in its separate entity can be a organizational/bookkeeping hassle but may protect you more based on if someone sued one of the LLCs.