I can have someone periodically clean them up.. would that be more cost-effective than spending it on gutters?

The time you spend on your marketing business is time you could've spent learning or networking in real estate.

We set aside a portion of our gross rents each month (usually 15-20%) in a capital improvement account and then we can use that account to fund repairs like roofs, AC units, remodel of kitchens or bathrooms, new appliances etc.You will always find something to spend on , I would spend some time to prioritize your capital spending, and to plan ahead of time for big ticket items to keep your place in top condition.  

However, your time is precious, and you don't want to spend it chasing people down all the time.

Remember that most HML rehab loans are given in reimbursement draws, so you're required to spend your own capital on rehab first and make progress before they will give you that money.Depending on where the property is, you may be able to get the same terms with only 10% down. 

2024 is 6 years awayI plan to spend the next 6-12 months learning and studying dealsI estimate that in order to replace ~$130,000 of gross annual income I will need to have that same total of net cash flow from my properties by that time (I currently only own two single family houses)If I make the assumption that the deals that I find/buy return $500 per month of net cash flow then I will need a total of 22 properties to equal $132,000 per year (22 * $500 = $11,000/mo. * 12mos = $132,000/yr)The $500 per unit estimate is not a per door estimate, rather a per unit estimate.

But before you make that decision, you need to have a serious come to jesus about what your goals, needs, and deal breakers are with regard to:Time - how much time can you reasonably afford to spend on the investment once it's made, on an ongoing basis Control - are you willing to sacrifice a bit of your return for someone else to handle tenanting, maintenance, and turnover, or do you want maximum control regardless of your experience levelResolve - if you're inclined to be very hands-on, do you honestly know that you will be able to maintain the level of involvement long-term?

I would be investing out-of-state though I plan to spend a few weeks there looking at properties and learning the area if everything pans out.

Definitely spend some time looking into other inspectors in your area before hiring someone for your next purchase.  

I want to diversify in a couple different locations and would be willing to spend 250,000-500,000 in each location.