When is it safe to start "paying yourself" from cash flow?

[Jeffrey D. Logan]

Hi all,

First time landlord in the Boston area here. Quick background: wife and I are moving to NH after being in a Somerville condo for 3 years. It has appreciated about $130k since we bought it ($570k to ~$700k). We were able to keep the condo and rent it out and it should cash flow (after mortgage, taxes, HOA and all expenses) around $250 a month. Obviously won't be the greatest cash-on-cash return if i were buying solely for a rental property, but the plan is to try this out for a while while betting that appreciation in Boston market will continue. We'll re-evaluate next year and decide whether to pull out the equity we have and invest in cheaper markets where the cash on cash return would be greater.

Anyways, I've read "The Book on Rental Property Investing" just to give me some background on real estate investing in general and the advice there is to keep 6 months of full expenses in cash reserves. He also outlines later on in the book how to account for big ticket capital expenses from a monthly budgeting perspective. So my question is, when do you consider it safe to start reinvesting the cash flow coming in? If you've already got 6 months of reserves in the bank, does a quarterly distribution of the cash above that make sense (where it could then either be re-invested into something else or saved for another downpayment)? Or should you just keep piling on the reserves for when that big ticket item like a new roof comes in? And how do you guys account for those unrealized, large expenses when analyzing your investment performance where you had budgeted for those expenses but haven't actually realized them yet (e.g. I've been budgeting for a new roof for 3 years but have not actually realized that expense yet and have actually re-invested some of the cash that would have otherwise gone towards that because I have enough in reserves)? 

Thanks and looking forward to being a part of the BiggerPockets community!

JD