It's hard for anyone to grow a portfolio with only negative cash flow properties (in growth markets).

I usually text stop. or block it. annoying but I guess hey if they get one its a win right.

Tha'ts usually an indicator of demand.

Does anyone have any negative/positive personal experiences with buying properties of this age

If my tenants have a good first year, before their notice is due, I send a renewal notice that has a 1-yr option near current market rents and a 2-yr option at slightly less, and I usually include a list of nearby rents so they can see they won’t get a better rate if they move.

Usually* less capital involved but you do need to be more careful on your exit options as far as lending for your end  buyer goes.

if cashflow is the goal, then a) choose a market to invest in that's cashflow-heavy, first and foremost. note: living in a property for a year doesn't necessarily build equity. your principle paydown year 1 ain't much & if the market dips a bit, you could have no or negative equity at the end of y1. just something to consider.note: appreciation in general is speculation. we can make educated guesses on what's going to happen, based on what HAS happened, but this isn't the 'perk of RE investing' to focus on when you know your goal is cashflow. ignore appreciation for now.if the goal is cashflow, why not just start with a rental?

I started in 2021 while being born and raised in San Francisco and found it really hard to find properties where the numbers and landlord laws actually made sense and I wasn't running a negative with only a hope and prayer that they would become cash flowing properties someday. 

Just remember: most negative reviews are written by problematic tenants.

DSCR loans are usually an easier underwrite that require less paperwork.