I started off with the standard turbo tax for 1099s and it felt limited.

I'm mostly a silent investor on that one, so I don't have much control over it.

I think every market and every person have their own reasons, but here are some thoughts from a property manager.Pros for self managing / cons of PM- Keep all the revenue- You have 100% control- You own listing, photos, etc- Nobody will ever care about your investment as much as you do.Cons for self managing/ Pros for property management- This is a 24h / 7days a week business and I imagine you have at least somewhat of a life I imagine. 

There's lots of opportunities in developing neighborhoods, but also seems a bit saturated at the moment.Also, definitely budget security (remote control cameras, alarm system, etc.) for your properties, as there are a lot of people who occupy themselves by breaking into houses and stealing anything they can sell.Lastly, there are a ton of contractors looking for a quick buck.

Again, expand your mind and break your internal idea limitations!

(check page 7 of this IRS Pub)Something that's non-passive and you materially participate means you can deduct those losses up to the excess business loss limit. 

Short term, leaving financing in place during rehab prior to resale — great strategy with limited risk to either party. 

Appreciation = Specilation/Gambling.We have little control over the factors that affect it, albeit for making improvements that will force it to compare with other likenpropetoes that are in a higher bracket.

got out of flipping to new construction in our market in columbus ohio. licensed general contractor. when interest rates got high single family existing went down by 30% new builds sold at a 6% increase that year which demonstrated the desire and premium that new construction commands. never looking back. total control, rinse and repeat. we can get permits in 28 days. we can buy land cash in 21 days. we can build in 120 days to 140 days and keep moving. super scalable and easy and no risk. we build the same 2-3 Floorplans 

And they remain owner and control the funding aspects.